Stereoselective 1,5-rearrangement of vinylketene-N,O-acetals: Novel vinylogous Ferrier reaction

Masaharu Inui, Seijiro Hosokawa, Atsuo Nakazaki, Susumu Kobayashi

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Vinylketene-N,O-acetals underwent Lewis acid-induced 1,3- or 1,5-rearrangement to afford the corresponding C-alkylated products. 1,5-Rearrangement proceeded predominantly in dichloromethane, and it is quite interesting to achieve an unprecedented high degree of asymmetric induction in such a remote position. Crossover experiments indicated that the reaction proceeded through an ion pair intermediate.

Original languageEnglish
Pages (from-to)3245-3248
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number18
DOIs
Publication statusPublished - 2005 May 2

Keywords

  • 1,5-Rearrangement
  • Lewis acid
  • Vinylketene-N,O-acetal
  • Vinylogous Ferrier reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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