A theoretical investigation of the facial selectivity of optically active oxazolidin-2-one-substituted dienes has been realized. This analysis enabled the development of (R)-4-phenyloxazolidin-2-thione as a very effective chiral auxiliary for cycloaddition of 1-aminodiene.

Reaction of 1-Aminodiene. -Theoretical and experimental studies indicate that (R)-4-phenyloxazolidin-2-thione is an efficient chiral auxiliary for cycloaddition of 1-aminodienes. It gives better stereoselectivity than the corresponding oxazolidin-2-one. -(ROBIETTE, R.; CHEBOUB-BENCHABA, K.; PEETERS, D.; MARCHAND-BRYNAERT*, J.; J. Org. Chem. 68 (2003) 25, 9809-9812; Unite Chim. Org. Med., Univ. Cathol. Louvain, B-1348 Louvain-la-Neuve, Belg.; Eng.) -Jannicke 17-115