A series of N 4 -substituted oxadiazinanones have been synthesized from (1R,2S)-norephedrine by a process of either reductive alkylation or arylation, N-nitrosation, reduction and cyclization. These derivatives (R = -CH 2 Ph, -CH 2 C(CH 3 ) 3 , -cyclo-C 6 H 11 , -C 6 H 5 ) have been acylated with propanoyl chloride and employed in the asymmetric Aldol reaction. The observed diastereoselectivities for the formation of the "non-Evans" syn-adduct ranged from 88:12 to 99:1. The hydrolysis of the Aldol adducts varied with the nature of the nitrogen substituent.

Other 6-membered heterocycles R 0670Synthesis, Asymmetric Aldol Reactions, and X-Ray Crystallography of Some Oxadiazinanone Derivatives. -Oxadiazinanones (V), synthesized from norephedrine, can be successfully employed in asymmetric aldol reactions. "non-Evans" syn-adducts (IX) (13 examples) are obtained with 76-98% d.e. Hydrolysis varies with the nature of the nitrogen substituent. -(HITCHCOCK*, S. R.; DAVIS, R. A.; RICHMOND, D. M.; DORE, D. D.; KUSCHEL, S. L.; VAUGHN, J. F.; WOLFE, J. A.; HAMAKER, C. G.; CASPER, D. M.; DINGLE, J.; J. Heterocycl. Chem. 45 (2008) 5, 1265-1274; Dep. Chem., Ill. State Univ., Normal, IL 61790, USA; Eng.) -D. Singer 06-175