Nucleophilic Cleavage of (2S,3S)-3-Phenylglycidol

Abstract

Reaction of (2S,3S)-3-phenylglycidol wlth a variety of nucleophiles has been examined.The reaction occurred regioselectively at the benrylic center generally with an excellent diastereoselectivity.Although most of the nucleophiles yielded the products with inversion of the original chirality, trimethylaluminum furnished the retention product in a high diastereoselectlvity.