Asymmetric synthesis of methylenecyclobutanes and their transformation to medium-sized carbocyclic compounds

Koichi Narasaka, Kazuhiro Hayashi, Yujiro Hayashi

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

The catalytic asymmetric [2+2] cycloaddition proceeds between 3-(2-alkenoyl)-1, 3-oxazolidin-2-ones and 1, 2-propadienyl sulfides having various substituents at 1-position, affording methylenecyclobutane derivatives with high optical purity. Seven and eight membered carbocycles with chiral side chains are prepared by the ring cleavage reaction and successive cationic cyclization of the chiral methylenecyclobutane derivatives having ω-alkenyl substituents.

Original languageEnglish
Pages (from-to)4529-4542
Number of pages14
JournalTetrahedron
Volume50
Issue number15
DOIs
Publication statusPublished - 1994 Apr 11
Externally publishedYes

Keywords

  • catalytic asymmetric [2+2] cycloaddition reaction
  • cationic cyclization
  • chiral titanium reagent
  • methylenecyclobutanes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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