Simple large-scale preparation of 3,3-disubstituted cyclopropenes: Easy access to stereodefined cyclopropylmetals via transition metal-catalyzed hydrometalation

Michael Rubin, Vladimir Gevorgyan

Research output: Contribution to journalArticle

48 Scopus citations

Abstract

3,3-Disubstituted cyclopropenes have been readily prepared in a multigram scale via two different methods: (1) dehydrohalogenation of bromocyclopropanes, and (2) Rh-catalyzed addition of carbenoids to trimethylsilylacetylene followed by desilylation. Highly diastereoselective Pd-catalyzed hydrostannation and highly enantioselective Rh-catalyzed hydroboration of 3,3-disubstituted cyclopropenes afforded useful cyclopropylmetal building blocks in high yields.

Original languageEnglish (US)
Pages (from-to)796-800
Number of pages5
JournalSynthesis
Issue number5
StatePublished - Apr 2 2004
Externally publishedYes

Keywords

  • Cyclopropane
  • Cyclopropene
  • Hydroboration
  • Hydrostannation
  • Transition metal catalysis

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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