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

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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

67 Citations (Scopus)

Abstract

Conjugate addition of lithium (S)-N-benzyl-N-a-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.

Original languageEnglish
Pages (from-to)1387-1394
Number of pages8
JournalOrganic and Biomolecular Chemistry
Volume2
Issue number9
DOIs
Publication statusPublished - 7 May 2004

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