Asymmetric synthesis and applications of β-amino Weinreb amides: asymmetric synthesis of (S)-coniine,10.1039/B402531H

热搜：

Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

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

Organic & Biomolecular Chemistry Pub Date : 04/05/2004 00:00:00 , DOI:10.1039/B402531H

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.