Stereospecific and Stereoselective Preparation of 2-(l-Hydroxyalkyl)-l-alkylcyclopropanols from alpha,beta-Epoxy Ketones and Bis(iodozincio)methane

摘要

The most common method used to prepare cyclopropane compounds involves the reaction of electrophilic Simmons-Smith-type reagents with alkenes.In contrast to this electrophilic [2+1] reaction,a gew-organodimetal compound also has the possibility of participating in a nucleophilic [2+1] reaction because it has two nucleophilic sites on one carbon atom.In fact,we have already reported the reaction of bis(iodozincio)methane(1)with 1,2-diketone to give cis-l,2-cyclopropanediol with high diastereoselectivity. In this transformation,1 acts as a bidentate Lewis acid and fixes the conformation of the 1,2-diketone in the s-cis form.