In situ generation of zinc carbenoids from diazo compounds and zinc salts: asymmetric synthesis of 1,2,3-substituted cyclopropanes

Sébastien R Goudreau; André B Charette

doi:10.1021/ja9074776

In situ generation of zinc carbenoids from diazo compounds and zinc salts: asymmetric synthesis of 1,2,3-substituted cyclopropanes

J Am Chem Soc. 2009 Nov 4;131(43):15633-5. doi: 10.1021/ja9074776.

Authors

Sébastien R Goudreau¹, André B Charette

Affiliation

¹ Department of Chemistry, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.

PMID: 19824678
DOI: 10.1021/ja9074776

Abstract

The first enantioselective cyclopropanation of alkenes using zinc carbenoids generated in situ from diazo compounds and zinc salts is reported. This new method allows the highly enantio- and diastereoselective synthesis of 1,2,3-substituted cyclopropanes via aryl-substituted carbenoids. The first Simmons-Smith reaction using a catalytic amount of zinc to generate enantioenriched cyclopropane is also reported.