Novel stereocontrolled synthesis of highly functionalized cyclobutanes by epoxide opening through a carbanion intermediate in heteroconjugate addition

Masaatsu Adachi, Eiji Yamauchi, Takema Komada, Minoru Isobe

Research output: Contribution to journalArticlepeer-review

22 Citations (Scopus)

Abstract

We have demonstrated a new cyclobutane ring formation from the trans-1,2-disubstituted epoxides through intramolecular carbanion opening process. In this reaction, the nucleophilic carbanion is generated not via α-proton abstraction but via heteroconjugate addition. These studies indicate that the different configuration of each epoxide (syn and anti) do not affect its reactivity and the reaction velocity in the cyclization step, providing multifunctionalized cyclobutanes in a regio- and stereospecific manner.

Original languageEnglish
Pages (from-to)1157-1161
Number of pages5
JournalSynlett
Issue number7
DOIs
Publication statusPublished - 2009 Apr
Externally publishedYes

Keywords

  • Cyclization
  • Cyclobutanes
  • Epoxides
  • Heteroconjugate addition
  • Sulfonyl carbanion

ASJC Scopus subject areas

  • Organic Chemistry

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