A Semi-Pinacol Rearrangement Approach to Bicyclo[3.2.1]octan-2-ones and Bicyclo[3.2.1]octan-3-ones

Abstract

A diastereoselective approach to bicyclo[3.2.1]octan-2ones and -3-ones is achieved by means of the semi-pinacol rearrangement of 2,3-epoxy silyl ethers. The key 1,2-migration is stereospecific. This method is easily amenable to an enantioselective synthesis by utilizing nonracemic norcamphor and related compounds.