Groups: Gaunt group website
Telephone:
01223 336364 (shared)
01223 336318
E-mail: mjg32@cam.ac.uk
NEW CATALYTIC STRATEGIES FOR CHEMICAL SYNTHESIS
Despite the changing face of chemistry, the importance of synthesis - the ability to generate molecules in a controlled fashion - has not diminished. However, the increasingly complex synthetic problems being posed by nature, medicine and materials demand new reactivity concepts and strategies in order to meet these challenges.
Our group is interested in the development of new catalytic strategies for chemical synthesis that engage novel reactivity concepts to enable the rapid generation of architecturally complex molecules and natural products. One of our key aims is to be able to construct natural products from simple building blocks in a single step, without the need for reactivity inducing functional groups and with the ability to control the stereochemistry.
In this way, we hope to be able to develop a chemo-catalytic equivalent to Nature's biosynthetic machinery that will enable us to build any molecule we want. Our approach to this is focussed on three main research programmes:
(A) metal catalyzed C-H bond functionalization,
(B) catalytic asymmetric synthesis using small molecule organic catalysts,
(C) cascade strategies for natural product synthesis.
In addition to this, many of the molecules that we are able to synthesise have interesting biological properties, and so we are also able to develop chemical biology applications from our synthetic chemistry projects.
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Gaunt Group
35. Angew. Chem. Int. Ed., 2011, 50, 1076-1079, Palladium(II)-Catalyzed C-H Bond Arylation of Electron-Deficient Arenes at Room Temperature DOI:10.1002/anie.201005990
34. Angew. Chem. Int. Ed., 2011, 50, 458-462, A Highly Para-Selective Copper(II)-Catalyzed Direct Arylation of Aniline and Phenol Derivatives DOI:10.1002/anie.201004703
33. Angew. Chem. Int. Ed., 2010, 50, 463-466, Copper(II)-Catalyzed meta-Selective Direct Arylation of α-Aryl Carbonyl Compounds DOI: 10.1002/anie.201004704
32. Chem. Sci., 2011, Advance Article, Amine directed Pd(II)-catalyzed C–H bond functionalization under ambient conditions DOI: 10.1039/C0SC00367K
31. Tetrahedron., 2010, 66, 6429, (invited submission for Tetrahedron Award, Symposium-in-print: Professor Steven V. Ley) Alkynes to (E)-enolates using tandem catalysis: stereoselective anti-aldol and syn-[3,3]-rearrangement reactions DOI: 10.1016/j.tet.2010.05.045
30. Science, 2009, 323, 1593, A Meta-Selective Copper-Catalyzed C–H Bond Arylation
DOI: 10.1126/science.1169975
This paper was featured in:
Perspectives in Science: Copper Puts Arenes in a Hard Position
RSC Chemistry World: Copper catalysts give meta aromatics
Research Highlights in Nature Chemistry: Electrophilic arylation: Substitution success
Chemical and Engineering News: Dodging The Substitution Laws
Science News: Helping Molecules Reach Meta
Angewandte Chemie: Meta-Selective Transition-Metal Catalyzed Arene C-H Bond Functionalization
This paper was voted as one of the top 12 papers of 2009 by Chemical and Engineering News Chemical Year in Review 2009.
29. J. Am. Chem. Soc., 2008, 130, 16184, Oxidative Pd(II)-Catalyzed C-H Bond Amination to Carbazole at Ambient Temperature DOI: 10.1021/ja806543s
28. J. Am. Chem. Soc., 2008, 130, 8172, Cu(II)-Catalyzed Direct and Site-Selective Arylation of Indoles Under Mild Conditions DOI: 10.1021/ja801767s
27. Angew. Chem. Int. Ed., 2008, 47, 3004, Synthesis of Rhazinicine by a Metal-Catalyzed C-H Bond Functionalization Strategy DOI: 10.1002/ange.200705005
26. J. Am. Chem. Soc., 2008, 130, 404, An Enantioselective Organocatalytic Oxidative Dearomatization Strategy DOI: 10.1021/ja077457u
25. Chem. Rev., 2007, 107, 5596, Recent Developments in the Use of Catalytic Asymmetric Ammonium Enolates in Chemical Synthesis DOI: 10.1021/cr0683764
24. Drug Discovery Today, 2007, 12, 8, Enantioselective Organocatalysis Review
DOI: 10.1016/j.drudis.2006.11.004
23. Angew. Chem., Int. Ed., 2006, 45, 6024, Enantioselective Catalytic Intramolecular Cyclopropanation using Modified Cinchona Alkaloid Organocatalysts DOI: 10.1002/ange.200602129
22. J. Am. Chem. Soc., 2006, 128, 2528, Mild Aerobic Oxidative Palladium (II) Catalyzed C-H Bond Functionalization: Regioselective and Switchable C-H Alkenylation and Annulation of Pyrroles
DOI: 10.1021/ja058141u
21. Angew. Chem., Int. Ed., 2006, 45, 2116, Organocatalytic Sigmatropic Reactions: Development of a [2,3] Wittig Rearrangement through Secondary Amine Catalysis DOI: 10.1002/anie.200504301
20. Angew. Chem., Int. Ed., 2005, 44, 3125, Palladium-Catalyzed Intermolecular Alkenylation of Indoles via Solvent-Controlled Regioselective C-H Functionalization DOI: 10.1002/anie.200500468
19. Angew. Chem., Int. Ed., 2004, 43, 4641, Enantioselective Organocatalytic Cyclopropanation via Ammonium Ylides DOI: 10.1002/ange.200460234
18. Angew. Chem., Int. Ed., 2004, 43, 2681, An Intramolecular Organocatalytic Cyclopropanation Reaction DOI: 10.1002/anie.200454007
17. Angew. Chem. Int., Ed., 2003, 42, 828, Organic-Catalyst-Mediated Cyclopropanation Reaction
DOI: 10.1002/anie.200390222
Postdoctoral Studies: Professor Steven Ley
16. J. Org. Chem., 2006, 7, 2715, Double Conjugate Addition of Dithiols to Propargylic Carbonyl Systems To Generate Protected 1,3-Dicarbonyl Compounds DOI: 10.1021/jo052514s
15. Synlett, 2005, 13, 2031, Synthesis of the EF Fragment of Spongistatin 1
DOI: 10.1055/s-2005-871960
14. Angew. Chem., Int. Ed., 2005, 44, 5433, Total Synthesis of Spongistatin 1: Exploiting the Latent Pseudo-Symmetry DOI: 10.1002/anie.200502008
13. Org. Lett., 2003, 5, 4819, Synthesis of C-1-C-28 ABCD Unit of Spongistatin 1
DOI: 10.1021/ol035849
12. Org. Lett., 2003, 5, 4815, A Practical and Efficient Synthesis of the C-16-C-28 Spiroketal Fragment (CD) of the Spongistatins DOI: 10.1021/ol035848h
11. Org. Lett., 2003, 5, 1147, Addition of Dithiols to Bis-Ynones: Development of a Versatile Platform for the Synthesis of Polyketide Natural Products DOI: 10.1021/ol034248f
10. Org. & Biomol. Chem., 2003, 1, 15, Development of β-Keto 1,3-Dithianes as Versatile Intermediates for Organic Synthesis DOI: 10.1039/b208982c
Postdoctoral Studies: Professor Amos Smith
9. J. Am. Chem. Soc., 2003, 125, 14435, Multicomponent Linchpin Couplings. Reaction of Dithiane Anions with Epoxides, Epichlorohydrin and Vinyl Epoxides: Efficient, Rapid and Stereocontrolled Assembly of Advanced Fragments for Complex Molecule Synthesis DOI: 10.1021/ja0376238
8. J. Am. Chem. Soc., 2002, 124, 14516, Dithiane Additions to Vinyl Epoxides: Steric Control over SN2 and SN2' Manifolds DOI: 10.1021/ja0283100
PhD Studies: Dr. Jonathan Spencer
7. Chemistry - A European Journal, 2006, 12, 949, Novel Anti-Markovnikov Regioselectivity in the Wacker Reaction of Styrenes DOI: 10.1002/chem.200400644
6. J. Org. Chem., 2002, 67, 4627, Convenient Preparation of Pure Trans-Arylalkenes via Palladium Catalyzed Isomerization of the Cis-Alkenes DOI: 10.1021/jo015880u
5. Chem. Comm., 2001, 1844, Evidence that the Availability of an Allylic Hydrogen Governs the Regioselectivity of the Wacker Oxidation DOI: 10.1039/b103066n
4. Org. Lett., 2001, 3, 25, Derailing the Wacker Oxidation: Development of a New Palladium Catalyzed Alkene Amination Reaction DOI: 10.1021/ol0066882
3. Org. Lett., 2000, 2, 1049, Selective Hydrogenolysis of Novel Benzyl Carbamate Protecting Groups
DOI: 10.1021/ol005589l
2. Tetrahedron Lett., 1999, 40, 1803, Preferential Hydrogenolysis of NAP Esters Provides a New Orthogonal Protecting group Strategy for Carboxylic Acids DOI: 10.1016/S0040-4039(99)00014-3
1. J. Org. Chem., 1998, 63, 4172, Rational Design of Benzyl Type Protecting Groups Allows Sequential Deprotection of Hydroxyl Groups by Catalytic Hydrogenolysis DOI: 10.1021/jo980823v
Non-profit:
Cancer Research UK, EPSRC, ERC, Leverhulme Trust, Marie Curie Foundation, Phillip & Patricia Brown
Other funding:
AstraZeneca, GlaxoSmithKline, Merck, Novartis, Pfizer Global Research, Syngenta
Biography:
Dr Matthew Gaunt graduated from the University of Birmingham with a BSc honours degree in Chemistry. He was awarded a PhD from the University of Cambridge after studies with Dr Jonathan Spencer, before moving to the University of Pennsylvania for postdoctoral studies with Professor Amos B Smith III, as a GlaxoWellcome Fellow. He returned to the UK as a Junior College Research Fellow with Professor StevenLey at the University of Cambridge in 2001. Dr Matthew Gaunt started his independent research career in October 2003 at the University of Cambridge. He was awarded a Royal Society University Research Fellowship from 2004-2009, and in October 2006 he was appointed as a Lecturer at the University of Cambridge. In October 2010 he was promoted to Reader in Chemical Synthesis. He currently holds an ERC Research Fellowship and an EPSRC Leadership Fellowship. Dr Gaunt has been the recipient of the AstraZeneca Research Award (2009), the Novartis Early Career Award for Organic Chemistry (2008-2011), the Eli Lilly Young Lecturer Award (2009), the Chemical Society Reviews Emerging Investigator Award (2009), and the Dow Pharma Prize for creativity in Chiral Chemistry (2005). He recently joined the Editorial Board of the RSC journal, Chemical Science as Associate Editor and is a member of the Scientific Advisory Board of Advanced Synthesis and Catalysis.
Awards:
Novartis Young Early Career Award in Organic Chemistry (2008-2011)
AstraZeneca Research Award (2009)
Chemical Society Reviews Emerging Investigator Award (2009)
Eli Lilly Young UK Lecturer Award (2008)
DowPharma Prize for Creativity in Chiral Chemistry in 2005