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Chromium-Mediated Stannylcyclopropanation of Alkenes with (Diiodomethyl)stannanes
Masahito Murai1, Ryuji Taniguchi1, Chisato Mizuta1
1Division of Applied Chemistry, Graduate School of Natural Science and Technology , Okayama University , 3-1-1 Tsushimanaka , Kita-ku , Okayama 700-8530 , Japan.
Abstract:
A stannyl-group-substituted gem-dichromiomethane species, generated in situ from CrCl2, TMEDA, and tributyl(diiodomethyl)stannane, worked as an efficient stannylcarbene equivalent to promote cyclopropanation of alkenes. The reaction provided synthetically useful stannylcyclopropanes directly from commercially available unactivated alkenes without using potentially flammable alkylzinc and diazo compounds. Structural characterization of stannyl- and germyl-group-substituted gem-dichromiomethane complexes and the effect of group 14 elements containing substituents for cyclopropanation are also described.
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