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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.

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The title compound, C13H18N2O2, is an N4-isopropyl-l-phenyl­alanine-based oxadiazinanone. Although the two mol­ecules in the asymmetric unit are oriented appropriately for hydrogen bonding, the distance between the donor and acceptor atoms is large enough to support only weak, if any, hydrogen bonding. The absolute configuration is known based on the known starting compounds in the synthetic procedure.