Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

Stephen G. Davies*, Keiji Iwamoto, Christian A.P. Smethurst, Andrew D. Smith, Humberto Rodriguez-Solla

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

71 Citations (Scopus)

Abstract

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

Original languageEnglish
Pages (from-to)1146-1148
Number of pages3
JournalSynlett
Issue number7
Publication statusPublished - 25 Jul 2002

Keywords

  • Asymmetric synthesis
  • Conjugate addition
  • Cyclic β-amino acids
  • Lithium amide
  • Ring closing metathesis

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