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The diastereoselective cyclopropanation of silyl-protected chiral allylic alcohols using Shi's carbenoid (TFA-Et(2)Zn-CH(2)I(2)) gave access to the anti-cyclopropylcarbinyl silyl ethers with excellent diastereocontrol. The level of stereocontrol was shown to depend on the sizes of the protective group and the allylic substituent. [reaction: see text]
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Charette et al. (2002) studied this question.
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