Asymmetric [2 + 2] Cycloaddition Reaction Catalyzed by a Chiral Titanium Reagent

Koichi Narasaka, Yujiro Hayashi, Hideshi Shimadzu, Shigeo Niihata

Research output: Contribution to journalArticlepeer-review

152 Citations (Scopus)

Abstract

In the presence of certain Lewis acids, alkenes containing an alkylthio group (for example, ketene dithioacetals, alkenyl sulfides, alkynyl sulfides, and allenyl sulfides) react with electron deficient olefins to give the corresponding cyclobutane, cyclobutene, or methylene cyclobutane derivatives. By employing a chiral titanium catalyst generated in situ from dichlorodiisopropoxytitanium and a tartrate-derived chiral diol, the [2 + 2] cycloaddition reaction proceeds with high enantioselectivity.

Original languageEnglish
Pages (from-to)8869-8885
Number of pages17
JournalJournal of the American Chemical Society
Volume114
Issue number23
DOIs
Publication statusPublished - 1992 Nov 1
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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