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(-)-8-Phenylmenthol was used as a chiral auxiliary to direct asymmetric reactions of its preformed carboxylates. Reduction of xanthates 1a and 1b by SmI 2 likely proceeded via HMPA-bound samarium enolate intermediates. Self- and cross-pinacolic coupling reactions of 8-phenylmenthyl α-oxoesters were achieved in a highly stereoselective manner by treatment with SmI 2 at -78 o ...
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