Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

A M Chippindale, S G Davies, K Iwamoto, R M Parkin, C A P Smethurst, H Rodrigues-Solla, Andrew David Smith

Research output: Contribution to journalArticlepeer-review

92 Citations (Scopus)

Abstract

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-alpha-methylbenzylamide to a range of alpha,beta-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic beta-amino esters in high d.e. Alternatively, conjugate addition to alpha,beta-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic beta-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)3253-3265
Number of pages13
JournalTetrahedron
Volume59
Issue number18
DOIs
Publication statusPublished - 28 Apr 2003

Keywords

  • lithium amide
  • conjugate addition
  • ring closing metathesis
  • OLEFIN METATHESIS
  • ENANTIOSELECTIVE SYNTHESIS
  • LITHIUM (ALPHA-METHYLBENZYL)ALLYLAMIDE
  • 2-SUBSTITUTED PIPERIDINES
  • ORGANIC-SYNTHESIS
  • STEREOSELECTIVE SYNTHESIS
  • TRANSANNULAR CYCLIZATION
  • (S)-HOMOPIPECOLIC ACID
  • NITROGEN-HETEROCYCLES
  • BICYCLIC LACTAMS

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