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The stereochemistry of attack on an allylsilane is more selective when the substituent on the chiral centre carrying the silyl group is larger than a methyl group, as shown by the reactions of the allylsilanes (5) and (12) with osmium tetroxide, m-chloroperbenzoic acid, and Yamamoto's methylenation reagent.
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Fleming et al. (1987) studied this question.
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