Diasteroselective Preparation of Cyclopropanols Using Methylene Bis(iodozinc)

A diastereoselective synthesis of trans-2-substituted cyclopropanols is outlined. Bimetallic CH2(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.本研究概述了反式2-取代环丙醇的非对映选择性合成方法。研究发现，双金属试剂CH₂(ZnI)₂可与α-氯代醛发生反应，生成环丙醇产物，产率介于64%至89%之间，非对映选择性比例（diastereomeric ratio，dr）≥10:1。该反应的高反式选择性源于环丙氧基中间体的平衡过程。