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Professor Matthew Gaunt

Portrait of mjg32

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.

Publications

Selective Reductive Elimination at Alkyl Pd(IV) via Dissociative Ligand Ionization Enables Catalytic C(sp3)–H Amination to Azetidines
MJ Gaunt, M Nappi, C He, W Whitehurst, B Chappell
– Angew Chem Int Ed Engl
(2018)
Enantioselective Copper-Catalyzed Arylation-Driven Semipinacol Rearrangement of Tertiary Allylic Alcohols with Diaryliodonium Salts.
DH Lukamto, MJ Gaunt
– Journal of the American Chemical Society
(2017)
139,
9160
Enantioselective Copper-Catalyzed Arylation-driven Semi-Pinacol Rearrangement of Allylic Alcohols with Diaryliodonium Salts
DH Lukamto, MJ Gaunt
– Journal of the American Chemical Society
(2017)
Palladium-catalyzed enantioselective C-H activation of aliphatic amines using chiral anionic BINOL-phosphoric acid ligands
AP Smalley, JD Cuthbertson, MJ Gaunt
– Journal of the American Chemical Society
(2017)
139,
1412
Ligand-assisted palladium-catalyzed C–H alkenylation of aliphatic amines for the synthesis of functionalized pyrrolidines
C He, MJ Gaunt
– Chem. Sci.
(2017)
8,
3586
Selective Palladium(II)-Catalyzed Carbonylation of Methylene β-C−H Bonds in Aliphatic Amines
JR Cabrera-Pardo, A Trowbridge, M Nappi, K Ozaki, MJ Gaunt
– Angew Chem Int Ed Engl
(2017)
56,
11958
Cobalt-catalysed C-H carbonylative cyclisation of aliphatic amides.
P Williamson, A Galván, MJ Gaunt
– Chem. Sci.
(2017)
8,
2588
The alpha-tertiary amine motif drives remarkable selectivity for Pd-catalyzed carbonylation of beta-methylene C-H bonds
KF Hogg, A Trowbridge, A Alvarez-Pérez, MJ Gaunt
– Chem. Sci.
(2017)
8,
8198
A general catalytic β-C-H carbonylation of aliphatic amines to β-lactams.
D Willcox, BGN Chappell, KF Hogg, J Calleja, AP Smalley, MJ Gaunt
– Science
(2016)
354,
851
Enantioselective Cu-Catalyzed Arylation of Secondary Phosphine Oxides with Diaryliodonium Salts toward the Synthesis of P-Chiral Phosphines
R Beaud, RJ Phipps, MJ Gaunt
– Journal of the American Chemical Society
(2016)
138,
13183
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Research Group

Research Interest Groups

Telephone number

01223 336318
36364 (shared)

Email address

mjg32@cam.ac.uk