Department of Chemistry

Dr Matthew Gaunt

The Gaunt Group

Telephone: 01223 336318

E-mail: mjg32@cam.ac.uk

(printable version)

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 of stereochemistry.

In this way, we hope to be able to develop a chemo-catalytic equivalent to Nature's biosynthetic machinery that we 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 also able to develop chemical biology applications from our synthetic chemistry projects.

Selected Publications

J. Am. Chem. Soc. (2008), 130, 8172. Cu(II)-catalyzed direct, site-selective arylation of indoles under mild conditions

Angew. Chem. Int. Ed. (2008), 47, 3004. Synthesis of Rhazinicine by a Metal- Catalyzed CH Bond Functionalization Strategy

J. Am. Chem. Soc. (2008), 130, 404, An Enantioselective Organocatalytic Oxidative Dearomatization Strategy

Chem. Rev. (2007), 107, 5596. Recent Developments in the Use of Catalytic Asymmetric Ammonium Enolates in Chemical Synthesis

Drug Discovery Today, (2007), 12, 8. Review: Enantioselective Organocatalysis

Angew. Chem. Int. Ed. (2006), 45, 6024. Enantioselective Catalytic Intramolecular Cyclopropanantion using Modified Cinchona Alkaloid Organocatalysts

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

Angew. Chem. Int. Ed. (2006), 45, 2116. Organocatalytic Sigmatropic Reactions: Development of a [2,3] Wittig Rearrangement through Secondary Amine Catalysis

Angew. Chem. Int. Ed. (2005), 44, 3125. Palladium-Catalyzed Intermolecular Alkenylation of Indoles by Solvent-Controlled Regioselective C H Functionalization