First evidence for the formation of a geminal dizinc carbenoid: A highly stereoselective synthesis of 1, 2, 3-substituted cyclopropanes

AB Charette, A Gagnon, JF Fournier

文献索引：Charette, Andre B.; Gagnon, Alexandre; Fournier, Jean-Francois Journal of the American Chemical Society, 2002 , vol. 124, # 3 p. 386 - 387

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被引用次数: 42

摘要

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.