Four stereogenic centers are generated with high diastereoselectivity in only a few steps starting from 2-naphthoic acid (1). Meyers oxazoline synthesis, nucleophilic addition of phenyllithium, and epoxidation afford rac-2 in 63% overall yield. The stereochemical course of the reaction is directed by the phenyl group.
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Linker et al. (1996) studied this question.
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