Chiral 1, 3-oxazolidines having a diphenylmethyl group at the 3-position of the oxazolidine ring as a bulky substituent were synthesized. The reaction of Grignard reagents with the chiral 1, 3-oxazolidines afforded the corresponding amines with very high diastereoselectivity. Furthermore, the method for the synthesis of optically active amines was applied to the asymmetric synthesis of (-)-dihydropinidine, a piperidine alkaloid.
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Yamauchi et al. (1998) studied this question.