Highly Enantio- and Diastereoselective One-Pot Synthesis of Acyclic Epoxy Alcohols and Allylic Epoxy Alcohols

摘要

In this report,we outline a highly enantio- and diastereoselective one-pot method for the efficient synthesis of synthetically useful acyclic epoxy alcohols and allylic epoxy alcohols.Our method takes advantage of a highly enantioselective C-C bond-forming reaction to set the initial chirality.The resulting allylic zinc alkoxide intermediate is then epoxidized in situ using either dioxygen or TBHP in the presence of a titanium tetraalkoxide.Epoxy alcohols with up to three contiguous stereocenters are formed in one pot with excellent enantio- and diastereoselectivity.In cases where the zinc alkoxide intermediates contain two different allylic olefins,the more electron-rich double bond is chemoselectively epoxidized to afford an allylic epoxy alcohol.This method represents a highly efficient,stereoselective,and chemoselective approach to the synthesis of a wide range of useful epoxy alcohol and allylic epoxy alcohol products that were previously difficult to access.