Issue 7, 2004
From the journal:

Organic & Biomolecular Chemistry

Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations

Andrew G. Brewster,b   Simon Broady,b   Catherine E. Davies (née Mills),a   Thomas D. Heightman,a   Stephen A. Hermitage,a   Mark Hughes,a   Mark G. Moloney*a  and  Gordon Woodsa  

* Corresponding authors

a The Department of Chemistry, Dyson Perrins Laboratory, The University of Oxford, South Parks Road, Oxford, UK
E-mail: mark.moloney@chem.ox.ac.uk

b AstraZeneca Pharmaceuticals, Mereside, Alderley Park, Macclesfield, UK

Abstract

The synthesis and alkylation of [4.3.0]-bicyclic lactams, derived from 6-oxopipecolic acid, have been investigated. Alkylation can proceed with predominantly exo-diastereoselectivity, but the efficiency of this process depends on the substitution at the hemiaminal ether system. These products can be readily deprotected to give substituted hydroxymethyl lactams in good yield.

Graphical abstract: Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations

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Article information

DOI
https://doi.org/10.1039/B316037H
Article type
Paper
Submitted
10 Dec 2003
Accepted
05 Feb 2004
First published
03 Mar 2004

Org. Biomol. Chem., 2004,2, 1031-1043

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Enantiopure bicyclic piperidinones: stereoselectivity in lactam enolate alkylations

A. G. Brewster, S. Broady, C. E. Davies (née Mills), T. D. Heightman, S. A. Hermitage, M. Hughes, M. G. Moloney and G. Woods, Org. Biomol. Chem., 2004, 2, 1031 DOI: 10.1039/B316037H

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