Cyclization of 1, n-enynes initiated by the addition reaction of gem-dichromiomethane reagents to alkynes

Masahito Murai, Ryuji Taniguchi, Kazuhiko Takai

Research output: Contribution to journalArticle

Abstract

Treatment of 1,n-enynes with gem-dichromiomethane species prepared in situ from 1,1-diiodomethanes and CrCl2 gave alkenylbicycloalkanes. Alkenylcarbene species, which was generated via [2 + 2] cycloaddition with a triple bond, were intercepted by intramolecular cyclopropanation of a pendant double bond, and alkene metathesis did not proceed. This is a very rare example of transformation of alkynyl CC with gem-dimetalloalkanes. Silyl- and borylcarbene equivalents generated from gem-(dichromio)silyl- and borylmethanes promoted the coupling and cyclization of enediynes as well as 1,n-enynes.

Original languageEnglish
Pages (from-to)3985-3988
Number of pages4
JournalOrganic Letters
Volume22
Issue number10
DOIs
Publication statusPublished - May 15 2020

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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