Abstract
Abstract The monoketal derived from cis-bicyclo[3.3.0]octane-3,7-dione was deprotonated using chiral lithium amide bases and the enolates were trapped as either enol acetates or trimethylsilyl enol ethers. Oxidative cleavage of the enol derivatives provided useful bicyclic lactones, the ee's of which could be determined using NMR chiral shift techniques. The lactones are also potentially useful as intermediates for asymmetric synthesis.
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