First evidence for the formation of a geminal dizinc carbenoid: a highly stereoselective synthesis of 1,2,3-substituted cyclopropanes.
Significant amounts of novel gem-dizinc carbenoids (RZnCHIZnR) are formed when diethylzinc is mixed with iodoform in CH2Cl2 at 0 degrees 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.
Charette
André B
AB
Département de Chimie, Université de Montréal, P.O. Box 6128, Station Downtown, Montréal, Québec, Canada H3C 3J7.
Gagnon
Alexandre
A
Fournier
Jean-François
JF
D003521:Cyclopropanes / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003521:Cyclopropanes