Chemistry–An Asian Journal

Stereospecific Construction of Chiral Tertiary and Quaternary Carbon by Nucleophilic Cyclopropanation with Bis (iodozincio) methane

K Nomura, S Matsubara

Index: Nomura, Kenichi; Matsubara, Seijiro Chemistry - An Asian Journal, 2010 , vol. 5, # 1 p. 147 - 152

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Citation Number: 12

Abstract

Abstract The reaction of a ketone having a leaving group at the α-position, such as α, β- epoxy ketone or α-sulfonyloxy ketone, with bis (iodozincio) methane affords a zinc alkoxide of cyclopropanol. The reaction proceeds by nucleophilic addition of the dizinc to the carbonyl group and a sequential intramolecular nucleophilic substitution of the introduced iodozinciomethyl group to the adjacent electrophilic carbon that has a leaving group. ...