External chiral ligand-induced enantioselective versions of the [2,3]- Wittig sigmatropic rearrangement

Katsuhiko Tomooka, Nobuyuki Komine, Takeshi Nakai

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The external chiral ligand-induced enantioselective [2,3]-Wittig rearrangements of crotyl benzyl ethers and crotyl propargylic ethers are described. The most notable is that treatment of (E)-crotyl propargylic ethers with a t-butyllithium/(S;S)-bis (oxazoline) complex provides a relatively high enantioselectivity (up to 89% ee), together with a high threo-diastereoselectivity. Furthermore, examples of the 'asymmetric catalytic version' of the rearrangement of crotyl benzyl ethers are presented. (C) 2000 Wiley-Liss, Inc.

Original languageEnglish
Pages (from-to)505-509
Number of pages5
JournalChirality
Volume12
Issue number5-6
DOIs
Publication statusPublished - 2000
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Catalysis
  • Pharmacology
  • Drug Discovery
  • Spectroscopy
  • Organic Chemistry

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