Synthesis,asymmetric aldol reactions,and x‐ray crystallography of some oxadiazinanone derivatives

A series of N₄‐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 = ‐CH₂Ph, ‐CH₂C(CH₃)₃, ‐cyclo‐C₆H₁₁, ‐C₆H₅) 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.