Lupton Group

Common Questions

• What is it like to do a PhD in Australia?
  PhDs in Australia normally take around 3.5 years. They are shorter than those in the US with fewer courses, so you spend most of your time on the project. For most students we aim to produce 3 papers from their studies. Scholarships are paid at around 31K Australian dollars tax free. In Melbourne that is enough to live comfortably, although many students also work as teaching assistants.
• Do you take international students?
  Yes we have taken students from many countries, i.e. China, India, New Zealand, Germany and the United Kingdom. Often 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.
• What do your students work as following graduation?
  Most of my graduate students have gone on to work in the chemical industry, agrochemicals or pharmaceuticals. Many are based abroad, in either Germany or the US, with the remainder in Australia. In most cases this is following a postdoctoral research fellowship.
• How hard is it to do a PhD?
  It is as hard as you make it. In general my students work in teams, and as a consequence the workload can be spread. With that said there are many times that a student strives to push their chemistry, and this requires a bigger effort.
• How big is the group?
  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.
• Will I love it?
  I would say yes. Australia is a diverse and multicultural place, and Melbourne is a very livable city. Our group is creative, resourceful, driven and looking forward to meeting you.

Publications (selected recent highlights)

• For complete publication records follow the links below.

• Google Scholar
• ORCID iD


#118. Radical coupling initiated by organophosphine addition to ynoates

Angew. Chem. Int. Ed. 2023, 62, e202303869

Jing Cao, Antonia Seitz, José A. Forni, Anastasios Polyzos,* David W Lupton*

In this study we were able to couple  nucleophilic organocatalysis possible with phosphines to redox chemistry triggered by photocatalysts and visible light. Central to this was appreciating the limitations introduced by this reaction design thus focusing studies on navigating a narrow window of reactivity. Conceived by Jing and I during one of Melbourne's  lockdowns and supported by our established collaboration with the Polyzos group this study came together nicely and was finished off by Toni in the early part of her PhD studies.



#109. Lewis Base Catalyzed Synthesis of Sulfur Heterocycles via the C1-Pyridinium Enolate

Angew. Chem. Int. Ed. 2022, 61, e202206647

Simon Cromwell, Randy Sutio, Changhe Zhang, Georgina Such, David W. Lupton*

We have a long standing interest in the use of  carbonyl surrogates in organocatalysis (i.e. Angew. 2015, 40, 11780). In this report we examine the use of thiocarbonyls in C1-Lewis base enolate based reactions as a new approach to sulfur heterocycles.  Fueled by observations from Changhe from  the Such lab, we have developed such chemistry allowing a range of common thiocarbonyls, well known in the controlled polymerisation community, to be reacted. Fantastic work during Randy's honours year and finished off by Simon.



#108. Enantioselective Synthesis of Pyrrolidines by a Phosphine-Catalyzed γ-Umpolung/β-Umpolung Cascade

Org. Lett. 2022 24, 2847

Jeremy T Maddigan-Wyatt, Jing Cao, Jhi Ametovski, Joel F Hooper, David W Lupton*

As part of a broader series of studies focused on the polarity inversion of conjugate acceptors using nucleophilic catalysis we report a reaction in which an allenoate undergoes polarity inversion at the b- and g-positions. This is a less common reactivity pattern than that seen in "Lu type" reactions involving allenoates and phosphines which generally engage as three carbon normal polarity dipoles. This is an older result from Jhi which required a bit of love from Jeremy leading to a nice little reaction, defining a good way to prepare enantioenriched pyrrolidines.



#104 Redox Isomerization/(3 + 2) Allenoate Annulation by Auto-Tandem Phosphine Catalysis

Chem.-Eur. J. 2021 27, 16232

Jeremy T Maddigan‐Wyatt, Mitchell T Blyth, Jhi Ametovski, Michelle L Coote, Joel F Hooper,* David W Lupton*

Developed alongside #108 this manuscript details an interesting example of auto-tandem phosphine catalysis. Specifically it was possible to couple a redox isomerization event which provides access a range of aliphatic imines  with a Lu type (3 + 2) annulation. Another project that we wrapped up through lockdown with really nice work from Mitchell in the Coote group providing some nice mechanistic rationales.



#101 Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

ACS Catal. 2020 10, 11791

Jing Cao, Rachel Gillard, Azar Jahanbakhsh, Martin Breugst, David W Lupton*

We have developed a range of reactions that exploit acyl fluorides as precursors to the acyl azolium using NHCs as organocatalysts (i.e. JACS, 2011, 133, 4694) . In this study we examine, in detail, the destination of the fluoride leaving group. As a result a new approach to the acyl azolium was uncovered with re-examination of a series of  earlier reactions, and some from other groups, demonstrating  generality. Key discoveries by Rachel and a lot of hard work by Jing, finished with some computational studies by our collaborator Martin Breugst and his student Azar.



#97 Enantioselective N‐Heterocyclic Carbene Catalyzed Bis (enoate) Rauhut–Currier Reaction

Angew. Chem. Int. Ed. 2019 58, 13370

Song Bae, Changhe Zhang, Rachel M. Gillard, David W Lupton*

The 1,4-addition of NHCs to conjugate acceptors has been a long standing interest of ours as it defines a useful route to polarity inverted reaction designs (i.e. Angew. 2016, 55, 3135). For many years we overlooked opportunities for reaction discovery with the initially formed enolate, the species responsible for the MBH and RC-reactions. In this study initiated by Changhe and fleshed out by Song an enantioselective RC reaction was possible with substrates that are unreactive  using more conventional phosphine organocatalysis. Some years later Venky was able to extend this concept to include amides (i.e. Org. Lett. 2021, 23, 9413).



#96 Enantioselective N-Heterocyclic Carbene Catalyzed (5+1) Annulations Exploiting a Vinyl Dianion Synthon Strategy

Angew. Chem. Int. Ed. 2019 58, 11483

Xuan Nguyen, Yuji Nakano, Nisharnthi M. Duggan, Lydia Scott, Martin Breugst, David W Lupton*

The 1,4-addition of NHCs to conjugate acceptors to invert polarity (i.e. Angew. 2016, 55, 3135) is exploited here in an unusual context. Drawing upon observations regarding the stability of Lewis base conjugate acceptor adducts we designed two reactions in which multiple C-C bond forming events can be conducted at the b-carbon. With one reaction we extend upon a family of substrates exploited in earlier studies(i.e. Angew. 2018, 57, 10299) while the second exploits a dimerizing desymmetrization. Really interesting reactivity, first uncovered by Yuji at the end of his PhD and developed further by Xuan with help from others, including  computational work from the Breugst lab.



#94 Enantioselective N‐Heterocyclic Carbene Catalysis that Exploits Imine Umpolung

Angew. Chem. Int. Ed. 2019 58, 4007

Jared E. M. Fernando, Yuji Nakano, Changehe Zhang, David W Lupton*

Our first study on the polarity inversion of carbonyl surrogates using NHC catalysis. Focusing on electron-poor imines it was possible to discover the first enantioselective reaction involving NHC mediated imine umpolung. A very thorough optimization was performed by Jared that allowed obserzations made by Yuji to be generalized. The result is a highly enantioselective reaction that allows access to a range of ketone type electron-poor imines.



#92 Enantioselective Total Synthesis of (−)-Δ9-Tetrahydrocannabinol via N-Heterocyclic Carbene Catalysis

Org. Lett. 2019, 21 , 1212

Adam Ametovski, David W Lupton*

We really enjoy performing studies in target synthesis, and have finished a few total syntheses off over the years (i.e. Angew. 2013, 52, 4113). In this report we take advantage of a method developed by Adam and Alison (i.e. Angew. 2016, 55, 16136) to access enantioenrioched cyclohexane derivatives. These were then elaborated to a range of THC molecules, including some derivatives.

Lupton Group Members

• We run a medium sized group made up of a healthy mix of international students, others from elsewhere in Australia or New Zealand, and a group from Monash.

Professor David W Lupton

David received his undergraduate education at the University of Adelaide (BSc Honours, 1st class) in 2001. In 2005 he completed PhD studies at the Australian National University (Professor Martin G. Banwell). Between 2005 and 2007, David was a postdoctoral fellow with Professor Barry M. Trost (Stanford University). In 2007, he commenced an academic appointment at Monash University, with promotion to Full Professor in 2018.

MAJOR AWARDS: • Birch Medal, RACI 2020 • Tarrant Lectureship, University of Florida 2018 • Alexander von Humboldt Ludwig-Leichardt Awardee 2015-2017 • Rennie Medal, RACI 2013• Future Fellowship, ARC 2011-2015 • Beckwith Lectureship, RACI 2012• Thieme journal award, 2012• Sir Keith Murdoch Postdoctoral Fellowship, 2005

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

Dr. Yuji Nakano

Yuji is an AMR fellow of Monash University with cosupervision by Greg Challis and Max Cryle. He completed his undergrduate at Monash University (BSc, Hons, 1st class)  in 2012 and his PhD in 2017 under the supervision of Professor David W. Lupton. Yuji then commenced postdoctoral studies with Professor Todd K. Hyster at Princeton University. Upon returning to Australia in 2019 he undertook further postdoctoral studies in medicinal chemistry with Professor Jonathan B. Baell at the Monash Institute of Pharmaceutical Sciences. Yuji’s main scientific interest lies in the use of novel and imaginative activation modes in reaction discovery. Yuji loves to gaze upon rocks, and eat plants.

Antonia Seitz

Antonia completed her Masters in chemistry at the Technical University of Munich under the supervision of Thorsten Bach. In 2022 she commenced studies at Monash University focused on phosphine organocatalysis.

James Shephard

James is a Victorian who completed his undergraduate with honours under the supervision of Alex Bissember, at the University of Tasmania  in 2021 (BSc, Hons, 1st class) . He commenced at Monash University in 2022 and is co-supervised by Alex. James likes big natural products and he cannot lie.

Chenxi (Aurora) Zhang

Aurora commenced her studies in our group in 2022 completing her (BSc, Hons, 1st class) later that year. In 2023 she commenced studies towards a PhD.

Qiang Meng

Qiang completed his Masters in chemistry at Lanzhou University with Professor Han before commencing studies towards his PhD at Monash University in 2019.

Andy Bartlett

Andy completed his undergrdauate studies at the University of Queensland in 2022 focused on medicinal chemistry before commencing studies at Monash University late in 2022.

Danae McCann

Danae commenced her honours in 2023. Over the next two years Danae intends to gain some deep insights into some of the more unusual reactions that we have discovered in recent years