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Chiral auxiliaries of the type Xc influence the pinacol coupling reaction of α-ketoamides in the presence of SmI2, hexamethyl phosphoramide, and tBuOH to give the pinacol products with high diastereoselectivity (up to >99%, see scheme). These products can then be hydrolyzed to give the enantiopure (S,S)- or (R,R)-2,3-dialkyltartaric acids. TBPS=tert-butyldiphenylsilyl.
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Kim et al. (2000) studied this question.
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