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Optically active α-siloxycarbonates are converted to optically active allylsulfides 1. These intermediates are allowed to react with dichloroketene (generated in situ) leading to optically active α,α-dichloro-β-vinyl-γ-siloxy-substituted thioesters 2. The assumed transition state is represented by 3. This ketene-Claissen rearrangement shows complete 1,2-asymmetric induction in all of the cases examined. Reductive dechlorination of the γ-siloxy-substituted thioesters provides optically active 3,4-cis-distubstituted γ-lactones. R = Me, iPr, C2H4OTBDMS; TBDMS = tert-butyldimethylsilyl.
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Nubbemeyer et al. (1991) studied this question.
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