Transition metal-catalyzed hydro-, sila-, and stannastannation of cyclopropenes: stereo- and regioselective approach toward multisubstituted cyclopropyl synthons

Marina Rubina; Michael Rubin; Vladimir Gevorgyan

doi:10.1021/ja027095k

Transition metal-catalyzed hydro-, sila-, and stannastannation of cyclopropenes: stereo- and regioselective approach toward multisubstituted cyclopropyl synthons

J Am Chem Soc. 2002 Oct 2;124(39):11566-7. doi: 10.1021/ja027095k.

Authors

Marina Rubina¹, Michael Rubin, Vladimir Gevorgyan

Affiliation

¹ Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607-7061, USA.

PMID: 12296700
DOI: 10.1021/ja027095k

Abstract

The first highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannation of cyclopropenes to give multisubstituted cyclopropylstannanes have been developed. It was shown that the addition across the double bond of cyclopropene is generally controlled by steric factors and proceeds from the least hindered face. The directing effect of alkoxymethyl substituents in the hydrostannation reaction of 3,3-disubstituted cyclopropenes was demonstrated. This methodology represents a powerful and atom-economic approach toward a wide variety of highly substituted cyclopropylstannanes, important building blocks unavailable by other methods.