Chiral dienolate chemistry in remote asymmetric induction: The allylation/Cope rearrangement sequence leading to γ-chiral α,β-unsaturated acid derivatives

Katsuhiko Tomooka, Atsushi Nagasawa, Shih Yi Wei, Takeshi Nakai

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The allylation of the dienolate derived from the chiral α, β- or β,γ-unsaturated imide followed by the Cope rearrangement is shown to effect the net remote asymmetric induction to create a new chirality of either configuration at the γ-position in high % de. The utility of this approach is shown in the asymmetric synthesis of the C6 side chain of zaragozic acid A. Copyright (C) 1996 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)8895-8898
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number49
DOIs
Publication statusPublished - Dec 2 1996
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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