Enantioselective Preparation of 8-Oxabicyclo[3.2.1]octane Derivatives via Asymmetric [3+2]-Cycloaddition of Platinum-Containing Carbonyl Ylides with Vinyl Ethers

Abstract

A catalytic asymmetric synthesis of 8-oxabicyclo[3.2.1]octane derivatives was achieved through the [3+2]-cycloaddition of the platinum-containing carbonyl ylides generated from acyclic gamma,delta-ynones on treatment with 10 mol % of PtCl(2)-Walphos and AgSbF(6). Synthetically useful 8-oxabicyclo[3.2.1]octane derivatives were obtained in good yields and mostly in over 90% ee's.