Desymmetrization of meso-1,2-, -1,3-, and -1,4-diols was performed by acylation with chiral twisted amides.1 The conformation of the twisted amides was studied by optimization of the PM3 method in order to elucidate the reaction mechanism. The directionality of the amide bond rotation was considered to be significantly responsible for the stereoselectivity.
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Yamada et al. (1998) studied this question.
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