Associate Professor Gareth Rowlands staff profile picture

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Associate Professor Gareth Rowlands PhD

Associate Professor

Institute of Fundamental Sciences

Dr. Gareth Rowlands is an Associate Professor of Chemistry at Massey University (2014). He joined Massey as a Senior Lecturer in 2006 after 7 years as a lecturer at the University of Sussex (UK). He has an interest in all aspects of organic chemistry. He can be found trying to spread his passion for organic synthesis in a number of chemistry's core papers and to a wider audience through a variety of review articles. His research focuses on chirality and stereoselective synthesis in all its forms. Much of this work has concentrated on the use of sulfoxides (his group was one of the first to report the use of sulfoxides in organocatalysis) and the chemistry of [2.2]paracyclophane but he has input into many different synthetic ventures through collaborations with his colleagues at Massey and elsewhere. One of these collaborations led him to become involved in the founding of Synthodics Ltd, a company set-up in conjunction with Massey colleagues to research new organic energy storage materials.

Gareth studied chemistry at Imperial College London, where he stayed to complete a PhD with Prof. Donald Craig. He then moved to Cambridge University as a Royal Commission for the Exhibition of 1851 Research Fellow, where he undertook a post-doc with Prof. Steven V. Ley CBE, FRS. In 1999 he started his independent research at the University of Sussex on the south coast of England. In 2006 he moved to the other side of the world and has been at Massey University in New Zealand ever since.

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Professional

Qualifications

  • BSc(Hons) - Imperial College London (1993)
  • Ph.D. - Imperial College London (1996)

Prizes and Awards

  • Industrial CASE Studentship Principle Investigator responsible for gaining competitive funding from GlaxoSmithKline PLC (Stevenage, UK) to cover the stipend of a Ph.D. student (‘Enantioselective nucleophilic catalysis with [2.2]paracyclophane-based heterocycles’ Andrew Hodgson, University of Sussex, 2008) and consumables of the value of GBP21,000. Resulted in one publication (Synlett, 2006, 2625). Proposals were peer reviewed by academics and researchers at GlaxoSmithKline PLC. - (2005)
  • Massey University Technicians Award Competitive internal funding was obtained to employ a technician for two years. The technician provided support for a range of synthetic projects synthetic projects culminating in two publications (Nominated Output 3 and 4), with more in preparation. Funding was awarded on the basis of external references and an internal interview process. - (2007)
  • EPSRC Grant EP/D50175X/1 Obtained GBP132,606 over three years through an open round of funding from the Engineering and Physical Sciences Research Council (UK) to fund research on Lewis basic organocatalysis (‘Chiral sulfinamides, N-oxides & beta-diketimines as Lewis base catalysts and Lewis bases in synthetic reactions; the development of new ligand systems’ Lamin Kamara, Ph.D. Thesis, University of Sussex, 2009). Resulted in two publications, NRO 3 (Chem. Commun. 2011, 47, 433) and Tetrahedron 2009, 65, 9134. Funding was awarded after peer review and ranking by a research council comprising of invited academics. - (2005)
  • Industrial CASE Studentship I was awarded a CASE award from GlaxoSmithKline (Stevenage, UK) that paid for one D.Phil. (Ph.D. student) and GBP21,000 worth of consumables over three years. I was the principle investigator. GSK PLC. From: GlaxoSmithKline PLC - (2003)
  • I was awarded an EPSRC grant for GBP62,765 for three years. I was the principle investigator. Engineering and Physical Sciences Research Council. From: EPSRC - (2002)
  • Massey University Postdoctoral Fellowship In conjunction with Dr. Vyacheslav Filichev, successfully bid for competitive funding to supported a postdoctoral fellow for two years. This permitted 'blue skies' research combining our expertise in DNA chemistry and asymmetric catalysis. Funding was awarded on the merit of external references and an internal interview process. - (2009)
  • I was jointly awarded an unrestricted grant for GBP5,000 from DuPont (USA) Ltd. I was co-investigator with Dr. Martyn P. Coles (University of Sussex, UK). From: DuPont Ltd. - (2003)

Research Expertise

Research Interests

Dr Gareth Rowlands' research is focused on chirality and asymmetric synthesis in all its forms (substrate control, chiral auxiliaries, reagent control and catalysis). We are interested in how stereochemical information is communicated between molecules and in 'non-traditional' forms of chirality, such as planar and axial chirality. Currently, research in the Rowlands' group is concentrating on the synthesis of [2.2]paracyclophane derivatives and their use in the design of new ligands and catalysts.

The synthesis of enantiomerically pure [2.2]paracyclophane derivatives – We are interested in developing new methodology for the synthesis of enantiopure [2.2]paracyclophanes; for the most part, this work focuses on the use of sulfoxides as temporary or traceless chiral auxiliaries that permit both the resolution of planar chirality and the functionalisation of the [2.2]paracyclophane backbone. We are also interested in other traceless auxiliaries for the resolution of planar chirality and these studies are directed towards the synthesis of heterocycles. Additionally, we would like to move away from using resolving agents and have started to investigate kinetic resolution of various [2.2]paracyclophane derivatives.

[2.2]Paracyclophane-based ligands and catalysts – We have a long-standing interest in the use of planar chiral phosphines as ligands for a variety of reactions. So far we have studied heterocyclic phosphines but current projects are looking at more basic phosphines. Heterocyclic derivatives have also been employed in Lewis basic catalysis. Finally, new methodology is allowing us to explore the use of various amino[2.2]paracyclophanes and this is opening up new and exciting avenues of research.

Thematics

Health and Well-being, Future Food Systems

Area of Expertise

Field of research codes
Chemical Science (030000): Organic Chemical Synthesis (030503): Organic Chemistry (030500)

Keywords

Organic synthesis, asymmetric synthesis, [2.2]paracyclophanes, asymmetric catalysis.

Research Projects

Summary of Research Projects

Position Current Completed
Project Leader 0 9

Completed Projects

Project Title: The first example of a chiral 1,2,3-triazolium N-hetercyclic carbene:synthesis and uses

Chirality ('handedness') is as old as life itself. Its importance is highlighted by 6 of the 8 top-selling medications being chiral, single-handed (enantiopure) molecules, including the cholesterol-lowering drug, Lipitor. One strand of our research studies the synthesis of new, single-handed molecules that have the potential to be used in asymmetric catalysis, the most efficient and elegant method for the preparation of chiral molecules. In this MURF-funded Summer Studentship we investigated a class of molecule known as N-hetereocyclic carbenes (NHCs). These small and simple molecules are highly reactive but offer many attractive features such as the ability to tune the reactivity of metal reagents and act as catalysts. Over the summer the student was able to prepare two new chiral NHCs and showed that they could form stable complexes with both palladium and gold, two metals that have been used extensively in catalysis. These preliminary results will be pursued in future projects with the hope of developing effective catalysts for the synthesis of biologically relevant molecules.
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Date Range: 2012 - 2012

Funding Body: Massey University

Project Team:

Project Title: Chiral [2.2] Paracyclophane Derivatives: a platform for new catalysts, materials and fundamental studies

Chirality is a concept central to chemistry, biology, argisciences/agrichemicals and pharmaceuticals. At its most basic level we all understand chirality. It is the difference between left and right hands; it is the fact that our left foot will only fit our left shoe. At a molecular level, chirality is exactly the same, one molecule will fit an enzyme and give a beneficial interaction while its mirror image does not. Worse still, the mirror image can actually cause unwanted effects as in the thalidomide catastrophe. One of the goals of our research is to use [2.2]paracyclophane as a platform to study both fundamental problems and tackle applied research related to the creation of chiral molecules. This MURF funding allowed us to employ a Research Technician to synthesize starting materials for the students tackling this research and, more excitingly, permitted a new method to be developed for the synthesis of planar chiral indoles; molecules that are of interest in both the preparation of new asymmetric catalysts and in medicinal chemistry.
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Date Range: 2012 - 2013

Funding Body: Massey University

Project Team:

Project Title: Planar chiral palladacycles

Many molecules are chiral, exhibiting mirror images (enantiomers) that only differ as our left and right hands are unlike. The effects of this disparity can be profound; for the drug ethambutol one hand treats tuberculosis and the other causes blindness. Asymmetric catalysis offers the most efficient and elegant method to prepare pure, single-handed molecules. In this project we were investigating the formation of chiral palladium containing molecules that had the potential to be used as asymmetric catalysts. The original summer studentship helped us prepare a mixture of left and right-handed catalysts. Since the completion of the studentship we have developed a procedure to separated these molecules (published in the Australian Journal of Chemistry) and have shown that they have the potential to catalyse valuable Suzuki-Miyaura coupling reactions.
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Date Range: 2010 - 2011

Funding Body: Massey University

Project Team:

Research Outputs

Journal

Jayasundera, KP., Kusmus, DNM., Deuilhé, L., Etheridge, L., Farrow, Z., Lun, DJ., . . . Rowlands, GJ. (2016). The synthesis of substituted amino[2.2]paracyclophanes. Organic and Biomolecular Chemistry. 14(46), 10848-10860
[Journal article]Authored by: Rowlands, G.
Thennakoon, N., Kaur, G., Wang, J., Plieger, PG., & Rowlands, GJ. (2015). An asymmetric variant of the Bischler-Möhlau Indole synthesis. Australian Journal of Chemistry. 68(4), 566-575
[Journal article]Authored by: Plieger, P., Rowlands, G.
Glover, JE., Plieger, PG., & Rowlands, GJ. (2014). An enantiomerically pure pyridine NC-palladacycle derived from [2.2]paracyclophane. Australian Journal of Chemistry. 67(3), 374-380
[Journal article]Authored by: Plieger, P., Rowlands, G.
Rowlands, GJ. (2013). Synthetic methods: Part (i) Free-radical reactions. Annual Reports on the Progress of Chemistry - Section B. 109, 88-102
[Journal article]Authored by: Rowlands, G.
Griffith, JA., Withers, JM., Martin, DJ., Rowlands, GJ., & Filichev, VV. (2013). Ligand assembly and chirality transfer guided by DNA modified with enantiomerically pure [2.2]paracyclophanes. RSC Advances. 3(24), 9373-9380
[Journal article]Authored by: Filichev, V., Rowlands, G.
Glover, JE., Martin, DJ., Plieger, PG., & Rowlands, GJ. (2013). Planar chiral triazole-based phosphanes derived from [2.2]paracyclophane and their activity in suzuki coupling reactions. European Journal of Organic Chemistry. (9), 1671-1675
[Journal article]Authored by: Plieger, P., Rowlands, G.
Rowlands, GJ. (2012). Synthetic methods part (i) free-radical reactions. Annual Reports on the Progress of Chemistry - Section B. 108, 15-28
[Journal article]Authored by: Rowlands, G.
Shaffer, KJ., Parr, DC., Wenzel, M., Rowlands, GJ., & Plieger, PG. (2012). The proton sponge effect: Substitution of quino[7,8-h]quinoline and the first structurally characterised derivatives. European Journal of Organic Chemistry. (35), 6967-6975
[Journal article]Authored by: Plieger, P., Rowlands, G.
Rowlands, GJ. (2012). Planar chiral phosphines derived from [2.2]paracyclophane. Israel Journal of Chemistry. 52(1-2), 60-75
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2011). Synthetic methods. Part (i): Free-radical reactions. Annual Reports on the Progress of Chemistry - Section B. 107, 19-33
[Journal article]Authored by: Rowlands, G.
Fulton, JR., Glover, JE., Kamara, L., & Rowlands, GJ. (2011). Facile synthesis of planar chiral N-oxides and their use in Lewis base catalysis. Chemical Communications. 47(1), 433-435
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2010). Synthetic methods: Part (i) free-radical reactions. Annual Reports on the Progress of Chemistry - Section B. 106, 19-33
[Journal article]Authored by: Rowlands, G.
Parmar, R., Coles, MP., Hitchcock, PB., & Rowlands, GJ. (2010). Towards a flexible strategy for the synthesis of enantiomerically pure [2.2]paracyclophane derivatives: The chemistry of 4-tolylsulfinyl[2.2] paracyclophane. Synthesis. (24), 4177-4187
[Journal article]Authored by: Rowlands, G.
Seacome, RJ., Coles, MP., Glover, JE., Hitchcock, PB., & Rowlands, GJ. (2010). Planar-chiral imidazole-based phosphine ligands derived from [2.2]paracyclophane. Dalton Transactions. 39(15), 3687-3694
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2010). Radicals in organic synthesis: part 2. Tetrahedron. 66(9), 1593-1636
[Journal article]Authored by: Rowlands, G.
Fulton, JR., Kamara, LM., Morton, SC., & Rowlands, GJ. (2009). The sulfinyl moiety in Lewis base-promoted allylations. Tetrahedron. 65(45), 9134-9141
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2009). Radicals in organic synthesis. Part 1. Tetrahedron. 65(42), 8603-8655
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2009). Synthetic methods: Part (i) free-radical reactions. Annual Reports on the Progress of Chemistry - Section B. 105, 19-34
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ., & Seacome, RJ. (2009). Enantiospecific synthesis of [2.2]paracyclophane-4-thiol and derivatives. Beilstein Journal of Organic Chemistry. 5
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2008). Synthetic methods: Part (i) Free-radical reactions. Annual Reports on the Progress of Chemistry - Section B. 104, 19-34
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2008). Enantioselective radical reactions and organocatalysis. Chemistry in New Zealand. 72, 92-96
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2008). The synthesis of enantiomerically pure [2.2]paracyclophane derivatives. Organic and Biomolecular Chemistry. 6(9), 1527-1534
[Journal article]Authored by: Rowlands, G.
Berry, MB., Craig, D., Jones, PS., & Rowlands, GJ. (2007). The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 3,
[Journal article]Authored by: Rowlands, G.
Berry, MB., Craig, D., Jones, PS., & Rowlands, GJ. (2007). The enantiospecific synthesis of (+)-monomorine I using a 5-endo-trig cyclisation strategy. Beilstein Journal of Organic Chemistry. 3
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2007). Synthetic methods: Part (i) Free-radical reactions. Annual Reports on the Progress of Chemistry: Section B. 103, 18-34
[Journal article]Authored by: Rowlands, G.
Hitchcock, PB., Hodgson, AC., & Rowlands, GJ. (2006). The first examples of planar chiral organic benzimidazole derivatives. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry. 2006(16), 2625-2628
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2006). Synthetic methods: Part (i) free-radical reactions. Annual Reports on the Progress of Chemistry, Section B, Organic Chemistry. 102, 17-33
[Journal article]Authored by: Rowlands, G.
Hitchcock, PB., Rowlands, GJ., & Seacome, RJ. (2005). The synthesis and directed ortho-lithiation of 4-tert-butylsulfinyl[2.2]paracyclophane. Organic and Biomolecular Chemistry. 3(21), 3873-3876
[Journal article]Authored by: Rowlands, G.
Hitchcock, PB., Rowlands, GJ., & Parmar, R. (2005). The synthesis of enantiomerically pure 4-substituted [2.2]paracyclophane derivatives by sulfoxide-metal exchange. Chemical Communications. 2005(33), 4219-4221
[Journal article]Authored by: Rowlands, G.
Griffith, JA., & Rowlands, GJ. (2005). The synthesis of novel 4-(aminomethyl)oxazoline ligands. Synthesis: Journal of Synthetic Organic Chemistry. 2005(19), 3446-3450
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2005). Synthetic methods: Part (i) Free-radical reactions. Annual Reports on the Progress of Chemistry, Section B, Organic Chemistry. 101, 17-32
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ., & Barnes, WK. (2004). Studies on the [2,3]-Stevens rearrangement of aziridinium ions. Tetrahedron Letters. 45(28), 5347-5350
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ., & Singleton, J. (2004). Activation by allylic alcohols of sulfur-containing dienes to ruthenium-catalysed ring-closing metathesis. Journal of Chemical Research. 2004(4), 247-251
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2004). Synthetic methods: Part (i) Free-radical reactions. Annual Reports on the Progress of Chemistry, Section B, Organic Chemistry. 100, 33-49
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ., & Barnes, WK. (2003). Chiral sulfoxides in the enantioselective allylation of aldehydes with allytrichlorosilane. Chemical Communications. 2003(21), 2712-2713
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2003). Synthetic methods: Part (i) Free-radical reactions. Annual Reports on the Progress of Chemistry, Section B, Organic Chemistry. 99, 3-20
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2003). Chiral sulfoxide ligands in catalytic asymmetric cyanohydrin synthesis. Synlett: Accounts and Rapid Communications in Synthetic Organic Chemistry. 2003(2), 236-240
[Journal article]Authored by: Rowlands, G.
Rowlands, GJ. (2001). Ambifunctional cooperative catalysts. Tetrahedron. 57(10), 1865-1882
[Journal article]Authored by: Rowlands, G.

Book

Rowlands, GJ. (2007). Product class 2: Hal/Hal acetals (Hal F). In SL. Warriner (Ed.) Science of Synthesis: Houben-Weyl Methods of Molecular Transformations. (pp. 63 - 115). Stuttgart, Germany: Georg Thieme Verlag
[Chapter]Authored by: Rowlands, G.

Conference

Martin, D., Rowlands, GJ., Thennakoon, N., & Wang, J. (2013, July). The design and synthesis of planar chiral phosphines derived from [2.2]Paracyclophane-based heterocycles. Presented at 6th Heron Island Conference on Reactive Intermediates and Unusual Molecules: Synthesis and Mechanism. Queensland, Australia.
[Conference Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2013, September). Addicted to base: Sulfoxides and N-oxides in asymmetric Lewis base catalysis. Presented at Department of Chemistry Postgraduate Symposium. Otago, New Zealand.
[Conference Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2013, December). The synthesis and resolution of planar chiral heterocycles derived from [2.2] paracyclophane. Presented at New Zealand Institute of Chemistry Conference 2013. Wellington, New Zealand.
[Conference Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2010, July). Chiral [2.2]paracyclophanes; synthesis and uses. Presented at 5th Heron Island Conference on Reactive Intermediates and Unusual Molecules: Synthesis and Mechanism. Heron Island, Great Barrier Reef, Queensland, Australia.
[Conference Oral Presentation]Authored by: Rowlands, G.
Parmar, R., Seacome, RJ., & Rowlands, GJ. (2009). Sulfoxides in the synthesis of chiral [2.2]paracyclophane derivatives. Poster session presented at the meeting of 21st International Symposium on Chirality. Breckenridge, Colorado, USA
[Conference Poster]Authored by: Rowlands, G.
Rowlands, GJ. (2008, November). An escape from 'flatland' chemistry: organic planar chirality. Presented at Chemistry and the Biosphere Conerence. University of Otago, Dunedin, New Zealand.
[Conference Oral Presentation]Authored by: Rowlands, G.
Withers, JM., Rowlands, GJ., & Filichev, VV. (2008). Fluorescent nucleotides utilizing [2,2]para-cyclophane for the detection of codon mismatches. Poster session presented at the meeting of Chemistry and the Biosphere Conference. Dunedin, NZ
[Conference Poster]Authored by: Filichev, V., Rowlands, G.
Rowlands, GJ. (2006, October). Lewis base catalysis: From sulfoxides to planar chirality. Presented at Royal Society of Chemistry One-Day Symposium: Organocatalysis. University College Dublin, Ireland.
[Conference Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2003, March). Sulfoxides in catalysis. Presented at Young Chemists 2003. London, UK.
[Conference Oral Presentation]Authored by: Rowlands, G.

Other

Rowlands, GJ. (2009, August). Chemistry through the looking glass. In The Royal Society of New Zealand and the Institute of Chemistry. Presented at Te Manawa, Palmerston North, New Zealand.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2008). Basic instincts: sulfoxides, allylation and planar chirality. Presented at The University of Auckland, Department of Chemistry.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2008). Basic Instincts: Sulfoxides, allylation and planar chirality. Presented at Wellington.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2008). [2.2]paracyclophane: Adventures with planar chirality. Presented at University of Waikato, Hamilton, NZ.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2007). What's the point? From point to planar chirality. Presented at Massey University, Palmerston North, NZ.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2006). So long and thanks for all the chemicals. Presented at University of Sussex, UK.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2005, October). Organic chemistry review lecture. In GlaxoSmithKline PLC. Presented at Harlow, UK.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2004). Towards a flexible strategy for the synthesis of [2.2]paracyclophane derivatives. Presented at King's College London, University of London, UK.
[Oral Presentation]Authored by: Rowlands, G.
Rowlands, GJ. (2004, September). Towards a flexible strategy for the synthesis of [2.2]paracyclophane derivatives. In Chiratech (DowPharma) Technologies Ltd. Presented at Cambridge, UK.
[Oral Presentation]Authored by: Rowlands, G.

Supervision and Teaching

Summary of Doctoral Supervision

Position Current Completed
Supervisor 2 0
CoSupervisor 5 2

Current Doctoral Supervision

Supervisor of:

  • Maulik Mungalpara - PhD
    New routes to planar chiral phosphorus ligands and their use in asymmetric catalysis
  • Leonie Etheridge - PhD
    Planar chiral amino acids as organocatalysts

CoSupervisor of:

  • Tyson Dais - PhD
    Development of 4f/3d heterodinuclear single molecule magnets: An experimental and computational study
  • Joel Cornelio - PhD
    Multicomponent Metal-Organic Frameworks
  • Rebecca Severinsen - PhD
    The Synthesis and Chemistry of New Ouino[7,8-h]quinoline Derivatives
  • David Nixon - PhD
    The Good without the Bad: Selective Chelators for Beryllium

Completed Doctoral Supervision

CoSupervisor of:

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