Issue 9, 2004
From the journal:

Organic & Biomolecular Chemistry

Asymmetric synthesis and applications of β-amino Weinreb amides: asymmetric synthesis of (S)-coniine

Anthony J. Burke,a   Stephen G. Davies,*a   A. Christopher Garner,a   Tom D. McCarthy,a   Paul M. Roberts,a   Andrew D. Smith,a   Humberto Rodriguez-Sollaa  and  Richard J. Vickersa  

* Corresponding authors

a Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, UK
E-mail: steve.davies@chem.ox.ac.uk

Abstract

Conjugate addition of lithium (S)-N-benzyl-N-α-methylbenzylamide to a range of α,β-unsaturated Weinreb amides proceeds with high levels of diastereoselectivity (>95% de). The β-amino Weinreb amide products may be transformed into β-amino ketones via reactions with Grignard reagents, while treatment with DIBAL-H furnishes β-amino aldehydes. Trapping of the aldehyde via Wadsworth–Emmons reaction and subsequent manipulation offers an efficient route to homochiral δ-amino acid derivatives and 2-substituted piperidines. The application of this methodology for the synthesis of (S)-coniine is demonstrated.

Graphical abstract: Asymmetric synthesis and applications of β-amino Weinreb amides: asymmetric synthesis of (S)-coniine

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Article information

DOI
https://doi.org/10.1039/B402531H
Article type
Paper
Submitted
19 Feb 2004
Accepted
22 Mar 2004
First published
05 Apr 2004

Org. Biomol. Chem., 2004,2, 1387-1394

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Asymmetric synthesis and applications of β-amino Weinreb amides: asymmetric synthesis of (S)-coniine

A. J. Burke, S. G. Davies, A. C. Garner, T. D. McCarthy, P. M. Roberts, A. D. Smith, H. Rodriguez-Solla and R. J. Vickers, Org. Biomol. Chem., 2004, 2, 1387 DOI: 10.1039/B402531H

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