STEREOSELECTIVE GENERATION OF 1-ACYLOXY-2-AMINO CARBANIONS BY DEPROTONATION - SYNTHESIS OF ENANTIOMERICALLY AND DIASTEREOMERICALLY PURE BETA-AMINO ALCOHOLS

Activation of the oxygen-substituted C atom so that it functions as a nucleophile-this is the key to the preparation of the stereoisomeric beta-amino alcohols in pure form. The stereochemical outcome of the reactions of O-carbamate derivatives of achiral 2-(dibenzylamino)alcohols (e.g. 1-->2) is determined by the reagent. If, on the other hand, a stereogenic center is in the beta position, the stereochemistry of the deprotonation and the substitution is determined by the substrate. In both cases, the configurationally stable alpha-acyloxy-beta-amino carbanion is the intermediate. El = electrophile.