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Abstract
Abstract A novel procedure for preparing trisubstituted ethylenes stereoselectively is based on the reaction of α-trialkylsilyl-substituted ketones with alkyllithium reagents and on the following highly discriminative elimination of the silyl and oxido (or hydroxyl) groups from the resulting adducts. The syn-elimination of both groups is observed under basic conditions, while the reaction proceeds in anti-fashion on acid treatment. Furthermore α-trimethylsilylated ketones are shown to be readily obtained from 2-trimethylsilyl-2,3-dialkyloxiranes. The reaction sequence is applied to the stereoselective synthesis of tetrahomonerol which has been obtained from the codling moth.
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