Research Overview

Enantioselective Catalysis

A broad and fundamental interest in catalysis is at the heart of all our research. Specifically we are intrigued by the ability to develop unknown reactions mainly in the areas of organocatalysis and transition metal catalysis.

Target Synthesis

Reaction discovery can, and should, play a transformative role in complex target synthesis. Many of our studies in target synthesis draw upon our synthetic methods, or alternately targets continue to inform methodological studies.

Synthesis Enabled Science

Advances in chemical synthesis have the potential to inform many aspects of science. We collaborate broadly to realise this and, for example, have looked at questions in magnetism, polymer science, and medicinal chemistry

ChemMedChem, 2019, 14, 527; Chem. Sci. 2018, 9, 7370; Adv. Biosys. 2018, 2, 1700240

Publications

Google ScholarORCID iDSCOPUS IDResearcher ID

83. Enantioselective N-heterocyclic carbene catalyzed bis(enoate) Rauhut-Currier reaction

Song Bae, Changhe Zhang, Rachel M. Gillard, David W. Lupton* Angew. Chem. Int. Ed. 2019, DOI: 10.1002/anie.201907111

Summary

Remarkably, the RC-reaction of (bis)enoate molecules remains a challenge in enantioselective catalysis. This may, in part, be due to the lower reactivity of such species compared to the more common (bis)enone substrates. In this publication we exploit highly nucleophilic NHCs to achieve enantioselective catalysis with bis(enoates). A nice substrate design from Changhe, with early discovery work, characterisation by Rachel, but really this was a big study by Song, who managed to push this one over the line just as his PhD came to a close. Congratulations Song.

82. N-Heterocyclic carbene catalyzed (5 + 1) annulations exploiting a vinyl dianion synthon strategy

Xuan B. Nguyen; Yuji Nakano; Nisharnthi M. Duggan; Lydia Scott; Martin Breugst; David W Lupton* Angew. Chem. Int. Ed. 2019, DOI: 10.1002/ange.201905475

Summary

A study that unfolded over a few years focused on the possibility that conjugate acceptor umpolung could be achieved multiple times. This would potentially provide a new avenue to fully substitiuted olefins from simple conjugate acceptors. Discoveries from Xuan and Yuji, with a nice colloration with Martin Breugst, allowed us to develop a series of (5 + 1) annulations.

  • Highlight in Chemistry in Australia

81. Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

Jared E. M. Fernando, Yuji Nakano, Changhe Zhang, David W. Lupton* Angew. Chem. Int. Ed. 2019, 53, 2905

Summary

Catalytic imine umpolung has only emerged as a synthetic strategy in recent years, with the first NHC mediated version reported in 2016 by A. T. Biju. In this study we were able to achieve an intermolecular and enantioselective reaction design through careful reaction design, discovery, and optimization by Yuji and Jared.

  • Selected as Hot Paper
  • Highlighted in SynFacts 2019 15 426
  • Highlighted in Chemistry In Australia

80. Rhodium catalyzed template-assisted distal para-C–H olefination

Uttam Dutta, Sudip Maiti, Sandeep Pimparkar, Siddhartha Maiti, Lawrence R. Gahan, Elizabeth H. Krenske, David W. Lupton* and Debabrata Maiti* Chem. Sci. 2019, DOI:doi.org/10.1039/C9SC01824G

Summary

Uttam and Sandeep, students cosupervised between the Maiti (IITB) and Lupton (Monash) labs of the Monash-IITB academy contributed to this study of Debs focused on directed para functionalisation using Rhodium catalysis.

Summary

Building on a strong methodological study (#62, Angew. Chem. Int. Ed., 2016, 55, 16374) led by Alison, Adam did some fantastic work to iron out a bunch of challenges. His work has resulted in a 10-step sequence that opens new opportunities for preparing unique THC analogs.

  • Top 20 most read Org. Lett. for March 2019

78. CryoEM‐Guided Development of Antibiotics for Drug‐Resistant Bacteria

Matthew J. Belousoff, Hari Venugopal, Alexander Wright, Samuel Seoner, Isabella Stuart, Chris Stubenrauch, Rebecca S. Bamert, David W. Lupton,* Trevor Lithgow* ChemMedChem 2019, 14, 527

Summary

Exploiting cryoEM derived structural information it was possible to develop simple linozelid analogs in which subtle stereoelectronic effects allowed conformational changes to a side chain. Great early synthetic work from Samuel (exchange from University of Vienna), cleaned up by Alexander, stay tuned for a more comprehensive study.

77. Enantioselective N‐Heterocyclic Carbene Catalyzed Cyclopentene Synthesis via the β‐Azolium Ylide

Lydia Scott, Yuji Nakano, Changhe Zhang, David W. Lupton* Angew. Chem. Int. Ed. 2018, 57, 10299.

Summary

Suprisingly simple to prepare substrates allowing access to highly enantioenriched cyclopentenes in as little as 5-steps. The second in our series of reactions involving conjugate acceptoir umpolung, discovered by Yuji and developed nicely by Lydia.

  • Highlighted by Douglas Taber in the Chemistry Portal

76. Enantioselective N‐Heterocyclic Carbene Catalysis via the Dienyl Acyl Azolium

Rachel Gillard, Jared E. M. Fernando, David W. Lupton* Angew. Chem. Int. Ed. 2018, 57, 4712

Summary

The first enantioselective reaction of the dienyl azolium. We first tried to access reactions of this type with Marcin in 2014 using a different reaction design (#48 Angew. Chem. Int. Ed., 2014, 53, 5314). Great perseverance from Rachel, supported by discovery work by Jared, allowed enantioselectivity to be achieved with this improved design. Some of my favourite examples allows tetracyclic products in less than 5-steps from commercial materials

  • Highlighted in Chemistry in Australia

75. RAFT polymer cross-coupling with boronic acids

Hartwig Golf, Riley O'Shea, Carl Braybrook, Oliver Hutt, David W. Lupton,* Joel F. Hooper* Chem. Sci. 2018, 9, 7370

Summary

A collaborative study with Joel Hooper focused on reimagining the RAFT end-group. In one step this undesirable functionality is replaced by an electron-rich arene, a nice route to functionalised polymers. Bodipy and biotin tagging was possible. Great work from Riley to make the original discovery as an undergraduate.

74. Hydrogel‐Immobilized Supercharged Proteins

Eleanor C. Campbell, Jacob Grant, Yi Wang, Mahakaran Sandhu, Richard J. Williams, David R. Nisbet, Adam W. Perriman,* David W. Lupton,* Colin J. Jackson* Adv. Biosystems 2018, 2, 1700240

Summary

A new approach to enzyme immobilization developed by the Jackson lab. Support from Jacob, allowed this new approach to be developed into a continuous flow process. Incredible turnover numbers, great recyclability, and high enantioselectivity.

73. Oxidative Cross-Coupling of Boron and Antimony Nucleophiles via Palladium(I)

Quillon Simpson, Matthew J. G. Sinclair, David W. Lupton, Adrian B. Chaplin* Joel F. Hooper* Org. Lett. 2018, 20, 5537

72. Use of the TCNQF42− Dianion in the Spontaneous Redox Formation of [FeIII(L−)2][TCNQF4⋅−]

Ian A. Gass,* Jinzhen Lu, Mousa Asadi, David W. Lupton, Craig M. Forsyth, Blaise L. Geoghegan, Boujemaa Moubaraki, John D. Cashion, Lisandra L. Martin, Alan M. Bond, Keith S. Murray* ChemPlusChem 2018, 83, 658

Summary

A Monash collaboration, with four groups contributing to this report led by Keith Murray. From our group Mousa played a key role in the ongoing delivery of novel persistent nitroxides.

  • Special issue in memory of Professor L. Spiccia

71. Quantification of the Michael-Acceptor Reactivity of α,β-Unsaturated Acyl Azolium Ions

Alison Levens, Feng An, Jared E. M. Fernando, Armin R. Ofial, David W. Lupton,* Herbert Mayr* Topics in Catalysis 2018, doi.org/10.1007/s11244-018-0914-5

Summary

Part of a larger collaboration with the Mayr labs (LMU) on the properties of catalysts and intermediates pivotal to NHC mediated reactions, in this report we clarify the impact of catalyst design on the electrophilcity of the unsaturated acyl azolium.

  • Dedicated to the memory of George A. Olah, creator of a new access to organic reactivity.

70. A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides

Milena L. Czyz, Geethika K. Weragoda, R. Monaghan, Timothy U. Connell, Martin Brzozowski, Andrew D. Scully, John Burton, David W. Lupton, Anastasios Polyzos* Org. Biomol. Chem. 2018, 19, 4456

69. Enantioselective N-Heterocyclic Carbene Catalyzed Synthesis of Functionalized Indenes

Changhe Zhang, David W. Lupton* Org. Lett. 2017, 16, 1543

Summary

A big study by Changhe, taking the acyl fluoride chemistry to the limit, with a broad range of bifunctional materials prepared and subjected to NHC-catalysis. A powerful route to more than 40 enantioenriched indenes.

68. N-Heterocyclic Carbene Catalysis via the α,β-Unsaturated Acyl Azolium

Changhe Zhang, Joel F. Hooper, David W. Lupton* ACS Catal. 2017, 7, 2583

Summary

A comprehensive review on the chemistry of the unsaturated acyl azolium.

  • ISI Highly cited.

67. Auxiliary-Directed C(sp3)-H Arylation by Synergistic Photoredox and Palladium Catalysis

Milena L. Czyz, David W. Lupton, Anastasios Polyzos* Chem.-Eur. J. 2017, 17, 14450

66. The redesign of oxazolidinone antibiotics in response to Staphylococcus aureus

David W. Lupton, Matthew J Belousoff* Future Microbiology 2017, 12, 1113

65. N-Heterocyclic Carbene Catalyzeed Transformylation

Jared E. M. Fernando, Alison Levens, Daniel Moock, David W. Lupton* Synthesis 2017, 49, 3505

Summary

A useful and general transformylation reaction that was well suited to a variety of alcohols, including hindered tertiary examples.

  • Special edition celebrating Prof. Herbert Mayr

64. Catalytic Arene meta-C–H Functionalization Exploiting a Quinoline Based Template

Uttam Dutta, Atanu Modak, Bangaru Bhaskararao, Milan Bera, Sukdev Bag, Anirban Mondal, David W. Lupton,* Raghavan B. Sunoj,* Debabrata Maiti* ACS Catal. 2017, 7, 3162

Summary

Great study from Uttam, a student of the Monash IITB academy.

63. Hexahalorhenate(IV) salts of metal oxazolidine nitroxides

Anders H. Pedersen, Blaise L. Geoghegan, Gary S. Nichol, David W. Lupton, Keith S. Murray, Jose Martinez-Lillo, Ian A. Gass, Euan K. Brechin* Dalton Trans. 2017, 46, 5250

Summary

Some work from Kim's honours year. Highly hindered imidazolylidene NHCs allowed a variety of Mukaiyama aldo and Michael chemistry to be achieved.

61. Enantioselective (4 + 2) Annulation of Donor–Acceptor Cyclobutanes by N-Heterocyclic Carbene Catalysis

Alison Levens, Adam Ametovski, David W. Lupton* Angew. Chem. Int. Ed. 2016, 55, 16374

Summary

The first enantioselective (4 + 2) annulation with a donor-acceptor cyclobutane. Alison covered a lot of ground in the early optimization before we really got a handle on the unique reactivity of these materials. Alison and Adam finished it up, paving the way for our later work on THC total synthesis.

  • Highlighted in Chemistry in Australia

60. Enantioselective N‐Heterocyclic Carbene Catalysis by the Umpolung of Unsaturated Ketones

Yuji Nakano, David W. Lupton* Angew. Chem. Int. Ed. 2016, 55, 3135

Summary

The first example in our series of studies on conjugate acceptor umpolung. This proved to be a really tricky reaction to crack. Many false leads, and a lost 6 months with some catalyst issues. In the end Yuji managed to get some great conditions locked down.

  • Highlighted in Chemistry in Australia

59. Influence of the N-Substituents on the Nucleophilicity and Lewis Basicity of N-Heterocyclic Carbenes

Alison Levens, Feng An, Martin Breugst, Herbert Mayr, David W. Lupton*Org. Lett 2016, 18, 3566

Summary

A great effort from Alison who was able to calculate nucleophilcity parameters for 4 common N-substituents in NHC catalysis. A real pleasure for both of us to work in Munich with the Mayr group, and great support from Feng.

58. All-carbon N‐Heterocyclic Carbene Catalyzed (3 + 2) Annulations using Donor-Acceptor Cyclopropanes

Lisa Candish, Rachel M. Gillard, Jared E. M. Fernando, Alison Levens, David W. Lupton*Isr. J. Chem. 2016 DOI: 10.1002/ijch.201500102

Summary

A personnal account of some of our studies on the use of Donor-Acceptor cyclopropanes in NHC organocatalysis. Hnbours to be invited by H.-U. Reissig and great to get to know D. B. Weix a few years later.

  • Invited Contribution, Special edition edited by Prof. H.-U. Reissig and Prof. Daniel B. Werz

57. Aryl Nitriles from Alkynes Using tert.-Butyl Nitrite: Metal-Free Approach to alkyne cleavage

Uttam Dutta, David W. Lupton,* Debabrata Maiti* Org. Lett. 2016, 18, 860

Summary

Not quite a first in class reaction but a pretty unusual transformation of an alkyne. Potentially applicable to the late stage introduction of nitrile functionality. One of the first papers from Deb and myself driven by the fantastic Uttam of the Monash-IITB academy.

  • Highlighted in C and E News

56. N‐Heterocyclic Carbene Catalyzed Synthesis of δ‐Sultones via α,β‐Unsaturated Sulfonyl Azolium Intermediates

Andrei Ungureanu, Alison Levens, Lisa Candish, David W. Lupton* Angew. Chem. Int. Ed. 2015, 54, 11780

Summary

Drawing upon the rich chemistry of sulfonyl fluorides originating in the Kodak labs in the 1970's, and a little ahead of the resurgence of interest in ESF, it was possible to develop a rare example of NHC organocatalysis that does not involve carbonyl compounds. One of Lisa's last studies, Andrei pushed it along, and Alison came in with some proof of principle enantioselectivity when we needed it most.

  • Highlighted in Chemistry in Australia

55. Enantioselective N-Heterocyclic Carbene Catalyzed Diene Regenerative (4 + 2) Annulation

Alison Levens, Changhe Zhang, Lisa Candish, Craig M. Forsyth, David W. Lupton* Org. Lett. 2015, 17, 5332

Summary

A follow up to one of our earlier diene regenerative (4 + 2) annulations, except with enantioselectivity and far simpler substrates. Alison and Changhe worked closely on this reaction allowing a nice route to enantioenriched cyclohexadienes.

54. Evaluation of reversible interconversion in comprehensive two-dimensional gas chromatography using enantioselective columns in first and second dimensions

Sabrina Kroger, Yong Foo Wong, Sung-Tong Chin, Jacob Grant, David W. Lupton, Philip J. Marriott J. Chromatogr. A 2015, 1404, 104

Summary

A Monash collaboration in which Jacob provided some pretty simple imines and their isomerism was studies using Phil's 2D GC strategies.

53. Electrosynthesis of Highly Transparent Cobalt Oxide Water Oxidation Catalyst Films from Cobalt Aminopolycarboxylate Complexes

Shannon A. Bonke, Mathias Wiechen, Rosalie K. Hocking, Xi-Ya Fang, David W. Lupton, Douglas R. MacFarlane, Leone Spiccia ChemSusChem, 2015, 8, 1394

52. N-Heterocyclic carbene catalysed redox isomerisation of esters to functionalised benzaldehydes

Lisa Candish, Alison Levens David W. Lupton* Chem. Sci. 2015, 6, 2366

Summary

A serendipitous discovey of a rare example of NHC redox isomerisation in which ester substrates give rise to aldehyde products. A lot of open questions in this reaction design which also allows a nice entry to axially chiral biaryls from point chiral b-lactones. Once more Lisa and Alison teamed up to drive this project forward.

  • Highlighted by Chemistry in Australia

51. The Regioselective Iodination of Quinolines, Pyridone, Coumarin and Uracil

Uttam Dutta, Arghya Deb, David W. Lupton*, Debabrata Maiti* Chem. Commun. 2015, 51, 17744

Summary

One of Uttam's first papers communicates a useful approach to the halogenation of various heterocycles.

50. Enantioselective All-Carbon (4 + 2) Annulation by N-Heterocyclic Carbene Catalysis

Lisa Candish,^ Alison Levens^ David W. Lupton* J. Am. Chem. Soc. 2014, 136, 14397 (^equal contribution)

Summary

While we had developed other (4 + 2) annualtions this one involves a subtle olefin isomerisation that allowed us to unlock very high levels of enantioselectivity, while keeping the b-lactone functionality intact. A consistently high performing reaction, scoping studies for this reaction in all cases gave fantastic results. Also one of Alison and Lisa's first studies together, of which many more would follow

  • Highlighted by Chemistry in Australia
  • Highlighted in Synfacts

49. Fukuyama Reduction and Integrated Thioesterification/Fukuyama Reduction of Thioesters and Acyl Chlorides Using Continuous Flow

Mousa Asadi, Shannon Bonke, Anastasios Polyzos,* David W. Lupton* ACS Catal. 2014, 4, 2070

Summary

The first Polyzos/Lupton collaboration played to the chemical engineering strengths of Mousa and allowed an integrated approach to the Fukuyama reduction under flow. The process avoids some of the technical limitations with this type of chemistry.

48. N-Heterocyclic Carbene (NHC) Catalysed Cascade Olefin Isomerisation Intramolecular Diels-Alder Reaction

Marcin Kowalczyk, David W. Lupton* Angew. Chem. Int. Ed. 2014, 53, 5314

Summary

Our first attempt at reaction discovery via a dienyl acyl azolium instead led to an unusual olefin isomerization Diels-Alder reaction. Patient work by Marcin got this study finalised, and a few years later underpinned our succussful use of the dienyl acyl azolium.

  • Highlighted in Synfacts 2014, 10 640
  • Highlighted by Chemistry in Australia

47. Solvate-Dependent Spin Crossover and Exchange in Cobalt(II) Oxazolidine Nitroxide Chelates

Ian A. Gass, Subrata Tewary, Goplan Rajaraman, Mousa Asadi, David W. Lupton, Boujemaa Moubaraki, Guillame Chastanet, Jean-Francois Letard, Keith S. Murray* Inorg. Chem. 2014, 53, 5055

Summary

Another installment from one of our most long running Monash collaborations.

46. Manganese(II) Oxazolidine Nitroxide Chelates: Structure, Magnetism, and Redox Properties

Ian A. Gass, Mousa Asadi, David W. Lupton, Boujemaa Moubaraki, Alan M. Bond, Si-Xuan Guo, Keith S. Murray* Aus. J. Chem. 2014, 67, 1618

Summary

A further report by Keith Murray and Ian Gass, now with Mousa Asadi from our group making the nitroxides.

Summary

An interesting side reaction that came about in some of our work on Pd-catalysed decarboxylative allylation.

44. Palladium[II] Catalysed C(sp3)-H Oxidation of Dimethyl Carbamoyl Tetrahydrocarbazoles

Yuji Nakano, David W. Lupton* Chem. Commun. 2014, 50, 1757

Summary

Yuji's undergraduate studies focused on the development of C-H oxidation approaches with hydrocarbazoles. Really nice work lead to a useful approach for the sp3 C-H oxidation directed by a dimethyl carbamoyl functionalised hydrocarbazole.

Summary

A review focused on highlighting the similarities and differences of Lewis base catalysis with some of the more common catalysts.

42. Iodobenzene-Catalyzed Oxabicyclo[3.2.1]Octane and [4.2.1]Nonane Synthesis via Cascade C–O/C–C Formation

Marsewi Ngatimin, Raphael Frey, Alsion Levens, Yuji Nakano, Marcin Kowalczyk, Kristina Konstas, Oliver Hutt,* David W. Lupton* Org. Lett. 2013, 15, 5885

Summary

A reaction designed and discovered by Raphael at the CSIRO, supervised by Oliver. Marsewi did a great job taking this proof of principle and turning into a general story. The reaction itself provides a great way to oxygen containing tetracycles, from simple monocyclic vinylogous esters.

41. N-tert-Butyl Triazolylidenes: Catalysts for the Enantioselective (3 + 2) Annulation of α,β-Unsaturated Acyl Azoliums

Lisa Candish, Craig M. Forsyth, David W. Lupton* Angew. Chem. Int. Ed. 2013, 52, 9149

Summary

In this manuscript we introduce a number of new N-substiuents on the morpholinone scaffold, and examine their use in ester oxidation state NHC catalysis. A very thorough piece of work, and our first enantioselective reaction design. This was late in Lisa's PhD and allowed the group to address enantioselectivity in most of the reactions that followed.

  • Highted by Chemistry in Australia

40. C–C Bond Fragmentation by Grob/Eschenmoser reactions, Applications in Dendrimer Synthesis

Judith Hierold, David W. Lupton* Org. Biomol. Chem. 2013, 11, 6140

Summary

Once more exploiting the Grob-Eschemoser fragmentation it was possible to assemble an array of dendrimers in a handful of steps. Judith also addressed some of the solubility issues with our earlier materials.

39. 1,3-Dihydro-4,5-dimethyl-1,3-bis(1-methylethyl)-2H-imidazol-2-ylidene

Alison Levens, Marcin Kowalczyk, David W. Lupton* eEros. 2013, https://doi.org/10.1002/047084289X.rn01656

Summary

IPrMe proved essential to a number of our organocatalytic processes (most notably: J. Am. Chem. Soc. 2011 133, 4694). In this report we discuss its preparation and use in catalysis.

Summary

A full report on Chris' communication on this topic.

  • Invited Contribution to SynthCon2 Research front

37. SynthCon2: A Forum for Australian Organic Chemists

David W. Lupton Aust. J. Chem. 2013, 66, 843

Summary

A research front highlighting chemistry from SynthCon2. This meeting was conceived by Richard Payne and myself during a trip to China. The focus then, and now, remains trying to create an open forum for Australian chemists to consider their science, and the unique challenges of working on this island continent.

36. Observation of Ferromagnetic Exchange, Spin Crossover, Reductively Induced Oxidation, and Field-Induced Slow Magnetic Relaxation in Monomeric Cobalt Nitroxides

Ian A. Gass, Subrata Tewary, Ayman Nafady, Nicholas. F. Chilton, Christopher J. Gartshore, Mousa Asadi, David W. Lupton, Boujemaa Moubaraki, Alan M. Bond, John F. Boas, Si-Xuan Guo, Gopalan Rajaraman, and Keith S. Murray* Inorg. Chem. 2013, 53, 7557

Summary

Another collaborative study using our nitroxide ligands and lead by Keith Murray and Ian Gass.

Summary

Embedded in a range of alkaloids is a chiral carbazole ring system. In this study we exploit readily accessable carbazolone derivatises as substrates in a Trost-Stoltz enantioselective decarboxylative allyalation. This allowed a formal synthesis of (-)-kopsihainanine A and has gone to enable the synthesis of related alkaloids.

  • Highlighted by Chemistry in Australia

34. Acyl Anion Free NHC-catalysis

Sarah, J. Ryan, Lisa Candish, David W. Lupton* Chem. Soc. Rev. 2013, 42, 4906

Summary

A review focused on reaction discovery with NHC organocatalysis in the absence of formation of the Breslow intermediate.

  • ISI highly cited publication
Summary

Our second study focused on considering the unsaturated acyl azolium as a system capable of reactions at the b-, a-, and acyl carbons. In this case a highly diastereoselective (3 + 2) annualtion was possible to give cyclopentyl b-lactones. Enantioselectivity was once more a challenge, but would soon be addressed.

  • Highlighted by Chemistry in Australia
  • Highlighted by Douglas Taber in the Chemistry Portal

32. 1,3-Dipolar Cycloaddition of Unstabilised Azomethine Ylides by Lewis Base Catalysis

Shveta Pandiancherri, Sarah J. Ryan, David W. Lupton* Org. Biomol. Chem. 2012, 10, 7903

Summary

Great mechanistic work, which I still use in undergraduate teaching, by Shveta in what proved to be a really challenging reaction design. While not the main focus of the study the first examples of reactions of the unsaturated acyl thiouronioum (adducts of isothiourea catalysts) are reported. This observation has been followed up by Andy Smith and Dan Romo with some really elegant reaction designs.

31. Synthesis of spirocyclic g-lactones by cascade Beckwith-Dowd ring expansion lactonization

Judith Hierold, David W. Lupton* Org. Lett. 2012, 14, 3412

Summary

As part of a study focused on developing new approaches to ethyl acorate we developed a Beckwith-Dowd ring expansion segwayed into a series of 5-exo radical cyclizations. Great solo work from Judith building on her earlier work on Grob-Eschenmoser fragmentations.

30. Synthetic and Quantum Mechanical Studies into the N-Heterocyclic Carbene Catalyzed (4 + 2) Cycloaddition

Sarah, J. Ryan, Andreas Stasch, Michael Paddon-Row,* David W. Lupton* J. Org. Chem. 2012, 77, 8831

Summary

Fantastic collaboration with Prof. Paddon-Row. The biggest outcome of this study was a far deeper appreciation of the decarboxylation chemistry. Exploiting this, a series of transformations with this key intermediate were possible.

Summary

Lisa's first reaction discovery. This is a really unusual transformation in which the NHC serves as both a Lewis and Bronsted base catalyst. Mechanistically we struggled with this for quite a while. A great conversation with SonBinh Nguyen (Northwestern), and some careful deuteration studies, were instrumental in allowing a viable mechanism to be devised.

  • Highlighted in the Chem. Sci. blog
  • Highlighted in Chemistry in Australia

28. Iodobenzene Catalysed Synthesis of Spirofurans and Benzopyrans by Oxidative Cyclisation of Vinylogous esters

Marsewi Ngatimin, Raphael Frey, Cecily Andrews, David W. Lupton,* Oliver E.Hutt* Chem. Commun. 2011, 47, 11778

Summary

Discvoered by Raphael under Oliver's supervision Marsewi was able to clean this study up and expand it. A really interesting reaction allowing various polycyclic oxygen containing heterocycles to be efficiently prepared.

Summary

In this second generation approach to the natural product many of the problems with our earlier synthesis are addressed allowing the target to be prepared in 10-steps.

Summary

An account regarding the discovery of the NHC catalysed (4 + 2) annualtion (J. Am. Chem. Soc., 2011, 133, 4694).

  • Some stuff
Summary

A lot of chemistry was developed to allow the related NHC catalysis (J. Am. Chem. Soc., 2011, 133, 4694) to be achieved. In this report we provide a thorough account of how the substrates, and other species, for this study can be prepared.

24. Chiral Lathanoid Dimers Ligated by Carbohydrate-based Diketonates: Catalytic and Luminescent Properties

YWilliam J. Gee, Judith Hierold, Jonathan G. MacLellan, Phillip C. Andrews, David W. Lupton, Peter C. Junk* Eur. J. Inorg. Chem. 2011, 25, 3755.

Summary

A collaborative study lead by Will from the Andrews/Junk group lead to some interesting coordination chemistry

23. N-Heterocyclic carbene catalyzed (4+2) Cycloaddition/ Decarboxylation of Silyl Dienol Ethers with a,b-unsaturated Acid Fluoride

Sarah, J. Ryan, Lisa Candish, David W. Lupton* J. Am. Chem. Soc. 2011, 133, 4694.

Summary

In this study it was possible to exploit the unsaturated acyl azolium as a conjugate acceptor and latent enolate. As a consequence bond formation was possible at the b-, a-, and acyl carbons. Specifically this allow the preparation of cyclohexenyl b-lactones which underwent decarboxyaltion to give cyclohexadienes.

  • Highlighted in Synfacts 2011, 5, 558
  • Highlighted in Chemistry in Australia

22. Anion Dependent Redox Changes in Iron Bis-terdentate Nitroxide {NNO} Chelates

Ian A. Gass, Christopher J. Gartshore, David W. Lupton, Boujemaa Moubaraki, Ayman Nafady, Alan M. Bond, John F. Boas, John D. Cashion, Carsten Milsmann, Karl Wieghardt, Keith S. Murray* Inorg. Chem. 2011, 50, 305

Summary

The first publication enabled by the oxazolidinone nitroxides prepared by Chris. Great to be able to support Ian and Keith by providing a simple ligand that gave them fascinating magnetism properties.

Summary

Building on our earlier dendrimer synthesis Judith was able to develop this fragementation chemistry into a general transformation. A very robust reaction as it turned out with more than 30 examples reported.

20. Preparation of 2-azaallyl anions and imines from N-chloroamines and their cycloaddition and allylation

Shveta Pandiancherri, David W. Lupton* Tetrahedron Lett. 2011, 52, 671

Summary

The chemistry of N-Cl compounds we first examined in the context of radical cyclisation chekmiostry. In this report we looked at their capacity to undergo halogen metal exchange and subseuqent b-hydride elimination. A really interesting report that unfortuantely became a neglected research area in the group.

19. Readily Accessible Oxazolidine Nitroxyl Radicals: Bifunctional Co-catalysts for Simplified Cu(II) based Aerobic Oxidation

Christopher J. Gartshore, David W. Lupton* Adv. Synth. Catal. 2010, 352, 3321

Summary

As part of attempts to achieve TEMPO based oxidations in an enantioselective fashion we examined the use of oxazolidinone based nitroxides in oxidation chemnistry. Unfortuantetyl, oxoammonium chemistry could not be accessed, although the use of Cu-based oxidation conditions allowed some reactions to be developed. This study also lead to a host of collaborative studies wuth the Murray and Bond/Martin groups focused on the use of these nitroxides as spin active ligands in association with cobalt and other spin active metals.

Summary

At the start of Lisa's PhD she finished off her undergraduate research project and developed this total synthesis. While the carbene chemistry reported the previous year (JACS, 2009, 131 14176) could be used we needed to resort to far less hindered catalysts to allow the key rearrangement to be achieved. Specifically we used the IPrMe catalyst, also known as Optimus Prime, which we discussed in in eEros a few years later.

17. A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclisation approach to C-3 mono-alkylated oxindoles and related compounds

Martin G. Banwell,* David T. J. Loong, David W. Lupton, David M. Pinkerton, Jayanta K. Ray, Anthonyl C. Willis Tetrahedron 2010, 47, 9252 (from PhD studies)

Summary

The last report from my PhD studies with our Pd-catalysed coupling chemistry now examined to make oxindoles.

16. A divergent synthesis of modular dendrimers via sequential C-C fragmentation thio-Michael addition

Judith Hierold, Angus Gray-Weale David W. Lupton* Chem. Commun. 2010, 46, 6789

Summary

Judith drove a very challenging project focused on the Grob-Eschenmoser fragmentation of simple b-keto esters. In this context it was possible to develop a new route to the preparation of dendrimers, including a G7 structures.

  • Highlighted in Synfacts 2010, 11, 1256

15. The discovery of catalytic enantioselective polyvalent iodine mediated reactions

Marsewi Ngatimin, David W. Lupton* Aust. J. Chem. 2010, 63, 653

Summary

As a part of Marsewi's PhD we reviewed the chemistry of enantioselective reaction discovery with polyvalent iodine.

Summary

Work from Sarah and Lisa's honours year projects make up the bulk of this report. This is an early example of NHC catalysis with ester oxidation state substrates, and the first NHC catalysed reaction of the unsaturated acyl azolium that involved conjugate addition. A very robust reaction that was even possible with moderate levels of enantioselectivity.

  • Highlighted in Chemistry in Australia

13. The a-halogenation of a,b-unsaturated carbonyls and dihalogenation of alkenes using bisacetoxyiodobenzene/pyride hydrohalides

Marsewi Ngatimin, Christopher J. Gartshore, Jeremy Kindler, Sudha Naidu, David W. Lupton* Tetrahedron Lett. 2009, 50, 6008

Summary

In a study that came about while I wasnt paying attention Jeremy looked at an oxidation in the presence of HCl salts. From this observation it was possible to develop an unusual route for generating chloronium ions and exploit them in chemistry.

12. A Synthetic and Computational Investigation into the Direct Synthesis of a-Hydroxylmethylated Enones from b-keto Phosphonates

Sarah, J. Ryan, Christopher D. Thompson, David W. Lupton* Aust. J. Chem. 2009, 62, 720

Summary

The groups first independent publication. As part of a broader idea in total synthesis we stumbled across, and somewhat reinvented, this interesting piece of olefination chemistry.

Supervised Publications

11. The synthesis of compounds related to the indole–indoline core of the vinca alkaloids (+)-vinblastine and (+)-vincristine

Michael J. Harvey, Martin G. Banwell*, David W. Lupton. Tetrahedron Lett. 2008, 49, 4780

10. Binuclear Zinc Catalyzed Aza-Henry reaction

Barry M. Trost*, David W. Lupton. Org. Lett. 2007, 9, 2023.

Summary

A relatively early example of the aza-Henry reaction. Using bimetallic catalysis it was possible to activate both coupling partners and deliver a highly enantioselective reaction.

9. Tandem Radical Cyclization reactions, initiated at Nitrogen, as an Approach to the CDE-tricyclic cores of certain post-Secodine Alkaloids

Martin G. Banwell*, David W. Lupton. Heterocycles 2006, 68, 71

Summary

An earlier strategy that I developed while Martin was an an AvH in Germany. In this work the great Athel Beckwith played a key advisory role, and in his humble way, made sure that the study had every chance to be succussfull.

Summary

The major component of my PhD studies. The synthesis was completed in the last months of my PhD and only with some great literature observations from my good friend Oliver Hutt, who I am lucky enough to continue to cllaborate with today.

Summary

The follow up to our indole synthesis this chemistry developed very quickly and introduced me to a wonderfully reliable haloformylation reaction that many of my students have subsequently revisited.

3. Synthesis of Indoles via Palladium[0]-Mediated Ullmann Cross-Coupling of o-Halonitroarenes with a-Halo-enones or -enals

Martin G. Banwell*, Brian D. Kelly, Okanya J. Kokas, David W. Lupton Org. Lett. 2003, 5, 2497.

Summary

A reaction discovery focused around increasing the efficiency of an early step in a multistep sequence. Was great to do the early optimisation and scope work and then to work with more experienced researchers to finalise the study.

Summary

Thanks to Natalie and Tom for letting me make a minor contrinbution to this study. My first taste of enantioselecrtive catalysis.

Summary

Reporting my honours work this publication describes some mechanistic work that I remain proud of today. The execution could be improved, but the appraoches are solid.

Research Group

Hayley Wilson

BSc Honours 2019

Darcy Williamson

PhD Scholar, 2019- [BSC Monash University, Lupton]

Simon Cromwell

PhD Scholar, 2019- [BSC Monash University, Chan]

Jing Cao

PhD Scholar, 2018- [MSC China Pharm. University, Du and Dong]

Jeremy Maddigan-Wyatt

PhD Scholar (with J. Hooper), 2019- [BSC Monash University, Lupton]

Xuan Nguyen

PhD Scholar, 2017- [BSC Monash University, Lupton]

Venkatachalam Pitchumani

PhD Scholar, 2017- [MSC University of Madras]

Alexander Wright

PhD Scholar, 2017- [BSC Monash University, Lupton]

Song Bae

PhD Scholar, 2016- [BSC Auckland University, Brimble]

Lydia Scott

PhD Scholar, 2016- [BSC Auckland University, Sperry]

About David

SUMMARY: David was born in South Australia, and recieved his undergraduate education at the Univeristy of Adelaide graduating with a BSc (Honours, 1st class) in 2001. In 2005 he completed his PhD studies at the Australian National University, supervised by Professor Martin G. Banwell. Between 2005 and 2007, Dr Lupton was a postdoctoral fellow with Professor Barry M. Trost (Stanford University) supported by the American Australian Association (Sir Keith Murdoch fellow). In 2007, he commenced an academic appointment at Monash University, receiving an Australian Research Council Future Fellowship in 2011 and promotion to Full Professor in 2018. His group is focused on the use of enantioselective catalysis to uncover novel reactivity and enable chemical synthesis.

MAJOR AWARDS: • Tarrant Lectureship, University of Florida 2018 • Alexander von Humboldt Ludwig-Leichardt Awardee (with Professor Herbert Mayr; LMU, Muenchen, Germany) 2015-2017 • Rennie Medal of the RACI 2013• Future Fellowship (FT110100319) 2011-2015 • Beckwith Lectureship of the RACI 2012• Thieme journal award of the Organic Editorial Board 2012• Monash Research Accelerator Program 2011-2012• Sir Keith Murdoch Postdoctoral Fellowship, American Australian Association 2005

EDUCATION: Postdoctoral Research Fellow, Department of Chemistry Stanford University, CA, USA. Supervisor: Professor Barry M. Trost Doctorate of Philosophy Research School of Chemistry, Australian National University, ACT, Australia. Supervisor: Professor Martin G. Banwell Bachelor of Science (Honours 1st) University of Adelaide, SA, Australia. Supervisor: Professor Dennis K. Taylor

CONTACT: david.lupton at monash.edu • twitter: @LuptonChemistry

full CV

Common Questions

PhDs in Australia normally take around 3.5 years. While theya re much shorter and those in the US there are fewer courses. So you spend most of your time working on a research project. For most students we aim to produce 3 or papers during their studies. Scholarships are paid at around 28K australian dollars tax free. In a city like Melbourne that is enough to live comfortably, although many students add to there salary through work as a teaching assistant.

Yes, we have taken students from many countries around the world, including: China, India, New Zealand, Germany and the United Kingdom. In many cases it is possible to secure scholarships to study at Monash regardless of your place of origin, however this requires high undergraduate marks and ideally some research experience. If you are from New Zealand then a special arrangement exists that means you are treated as an Australian student.
Most of my graduate students have gone on to work in the chemical industry, agrochemicals or pharmaceuticals. Many are based aborad, in either Germany or the US, with the remainder in Australia. In most cases this is following a postdoctoral research fellowship.
It is as hard as you make it. In general my students work in teams, and as a consequence the workload can be fairly spread. With that said there are many times that a student strives to push their chemistry, and this can require a bigger effort.
In general my group is normally under 10 people. This is a good number that allows me to supervise the projects in a meaningful way which helps increase productivity.