Issue 22, 2010
From the journal:

Organic & Biomolecular Chemistry

Rhodium-catalysed conjugate addition of arylboronic acids to enantiopure dehydroamino acid derivatives†

Jonathan D. Hargrave,a   Gerwyn Bish,b   Gabriele Kociok Köhna  and  Christopher G. Frost*a  

* Corresponding authors

a Department of Chemistry, University of Bath, Claverton Down, Bath, UK
E-mail: c.g.frost@bath.ac.uk
Fax: 01225 386231
Tel: 01225 386142

b Pfizer Limited, Ramsgate Road, Sandwich, Kent, UK

Abstract

The rhodium-catalysed conjugate addition of arylboronic acids to an enantiopure acceptor derived from (R)-S-methylcysteine proceeds under substrate control to provide a range of functionalised phenylalanine derivatives with excellent stereocontrol via a highly diastereoselective protonation.

Graphical abstract: Rhodium-catalysed conjugate addition of arylboronic acids to enantiopure dehydroamino acid derivatives

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Article information

DOI
https://doi.org/10.1039/C0OB00158A
Article type
Paper
Submitted
21 May 2010
Accepted
22 Jul 2010
First published
08 Sep 2010

Org. Biomol. Chem., 2010,8, 5120-5125

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Rhodium-catalysed conjugate addition of arylboronic acids to enantiopure dehydroamino acid derivatives

J. D. Hargrave, G. Bish, G. K. Köhn and C. G. Frost, Org. Biomol. Chem., 2010, 8, 5120 DOI: 10.1039/C0OB00158A

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