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Keywords:

  • asymmetric syntheses;
  • dihydrooxazoles;
  • epoxidations;
  • naphthalene derivatives;
  • synthetic methods
Thumbnail image of graphical abstract

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.