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First Evidence for the Formation of a Geminal Dizinc Carbenoid:  A Highly Stereoselective Synthesis of 1,2,3-Substituted Cyclopropanes

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posted on 2001-12-19, 00:00 authored by André B. Charette, Alexandre Gagnon, Jean-François Fournier
Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 °C. This reagent was shown to be effective in the cyclopropanation of butenediol derivatives to generate a cyclopropylzinc intermediate that could be trapped with a variety of electrophiles. 1,2,3-Substituted cyclopropane derivatives are formed with excellent diastereoselectivities by using this simple procedure.

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