Highly diastereo- and regioselective transition metal-catalyzed additions of metal hydrides and bimetallic species to cyclopropenes: Easy access to multisubstituted cyclopropanes

Alexander Trofimov, Marina Rubina, Michael Rubin, Vladimir Gevorgyan

Research output: Contribution to journalArticle

41 Scopus citations

Abstract

(Chemical Equation Presented) The first highly efficient, diastereo- and regioselective transition metal-catalyzed addition of metal hydrides (stannanes, silanes, and germanes) and bimetallic species (ditins and silyltins) to cyclopropenes has been developed. It was shown that the addition across the double bond of cyclopropenes is generally controlled by steric factors and proceeds from the least hindered face. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted stereodefined cyclopropylmetals, useful building blocks unavailable by other methods.

Original languageEnglish (US)
Pages (from-to)8910-8920
Number of pages11
JournalJournal of Organic Chemistry
Volume72
Issue number23
DOIs
StatePublished - Nov 9 2007
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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