Stereoselective production of beta-amino alcohols and beta-thioacyl alcohols via an application of the non-aldol aldol process

The mesylates used as protecting groups to permit the formation of bis(poly propionates) via the nonaldol aldol process can be easily displaced with go od nucleophiles, e.g., azide, thioacetate, acetate, to generate beta-azido (and beta-amino) alcohols, beta-thioacyl alcohols, and aldols of the opposi te chirality, e.g.,syn isomers afford anti products. Thus the anti mesylate 15 affords the all-anti mzido aldol system 16 in good yield. (C) 1999 Else vier Science Ltd. All rights reserved.