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Issue 9, 2004
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Asymmetric synthesis and applications of β-amino Weinreb amides: asymmetric synthesis of (S)-coniine

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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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Publication details

The article was received on 19 Feb 2004, accepted on 22 Mar 2004 and first published on 05 Apr 2004


Article type: Paper
DOI: 10.1039/B402531H
Citation: 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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