Issue 22, 2007
From the journal:

Organic & Biomolecular Chemistry

Stereocontrolled synthesis and alkylation of cyclic β-amino esters: asymmetric synthesis of a (−)-sparteine surrogate†‡

Jean-Paul R. Hermet,a   Aurélien Viterisi,a   Jonathan M. Wright,a   Matthew J. McGrath,a   Peter O'Brien,*a   Adrian C. Whitwood§a  and  John Gildayb  

* Corresponding authors

a Department of Chemistry, University of York, Heslington, York, UK
E-mail: paob1@york.ac.uk
Fax: +44 1904 432516
Tel: +44 1904 432535

b AstraZeneca, Process R & D, Avlon Works, Severn Road, Hallen, Bristol, UK

Abstract

A convenient method for the stereoselective synthesis of cyclic β-amino esters from an iodo αβ-unsaturated ester and α-methylbenzylamine is described. Subsequent enolate generation and alkylation proceeds with complete stereocontrol, with the two stereogenic centres working together. In this way, a functionalised piperidine suitable for alkaloid natural product synthesis was prepared. The usefulness of the methodology is exemplified with the concise synthesis of a (−)-sparteine surrogate.

Graphical abstract: Stereocontrolled synthesis and alkylation of cyclic β-amino esters: asymmetric synthesis of a (−)-sparteine surrogate

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Article information

DOI
https://doi.org/10.1039/B712503H
Article type
Paper
Submitted
14 Aug 2007
Accepted
20 Sep 2007
First published
02 Oct 2007

Org. Biomol. Chem., 2007,5, 3614-3622

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Stereocontrolled synthesis and alkylation of cyclic β-amino esters: asymmetric synthesis of a (−)-sparteine surrogate

J. R. Hermet, A. Viterisi, J. M. Wright, M. J. McGrath, P. O'Brien, A. C. Whitwood and J. Gilday, Org. Biomol. Chem., 2007, 5, 3614 DOI: 10.1039/B712503H

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