Diasteroselective Preparation of Cyclopropanols Using Methylene Bis(iodozinc)

Abstract

A diastereoselective synthesis of trans-2-substituted cyclopropanols is outlined. Bimetallic CH(2)(ZnI)(2) was found to react with α-chloroaldehydes to give cyclopropanols in yields of 64-89% and dr's ≥ 10:1. The high trans-selectivity resulted from equilibration of the cyclopropoxide intermediates.