Chiral oxazolidinones from alpha-hydroxy oxazolidines: a new access to 1,2-amino alcohols

N-Carbamoyl-alpha-hydroxy oxazolidines prepared from N-Boc-2-acyl oxazolidi nes or N-Boc-2-alkenyl oxazolidines, using phenyl glycinol as the chiral so urce, are converted into bicyclic oxazolidinones. Reactions of these compou nds with different nucleophiles under conditions suitable for the productio n of N-acyliminium ions were studied. Allylsilane reacted very stereoselect ively in all cases, and this reaction provides a new flexible entry for the preparation of enantiopure syn-2-amino alcohols, possibly bearing an addit ional stereocenter ex to the hydroxyl moiety. (C) 1998 Elsevier Science Ltd . All rights reserved.