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-2-ones 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.

rearrangement - ring expansion - epoxides - stereoselectivity

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<A NAME="RD14808ST-14">14</A>

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As 12 was found to be somewhat labile toward acid (e.g., SiO₂), it was isolated as the corresponding E-enone.