Hemiaminals as substrates for sulfur ylides: Direct asymmetric syntheses of functionalised pyrrolidines and piperidines

Christoforos G. Kokotos, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

48 Citations (Scopus)

Abstract

Phenyl stabilised chiral sulfur ylides react with five-membered-ring hemiaminals to give functionalised pyrrolidines directly with high enandoselectivity. The reaction can be diverted to give piperidines instead by isolation of the intermediate epoxide and treatment with TMSOTf.

Original languageEnglish
Pages (from-to)2156-2158
Number of pages3
JournalChemical Communications
Issue number20
DOIs
Publication statusPublished - 28 May 2006

Keywords

  • THROMBOXANE RECEPTOR ANTAGONIST
  • EPOXIDE OPENINGS
  • (+/-)-(5Z)-7-<3-ENDO-<(PHENYLSULFONYL)AMINO>BICYCLO<2.2.1>HEPT-2-EXO-YL>HEPTENO ACID
  • STEREOSELECTIVE-SYNTHESIS
  • TETRAHYDROPYRAN SYSTEMS
  • DERIVATIVES
  • 6-ENDO
  • 5-EXO
  • STEREOISOMERS
  • ACTIVATION

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