Asymmetrical nonbridgehead nitrogen-XXVI: Synthesis,configurational stability,and resolution of N,N-dialkoxyamines into antipodes

Alkoxyamines with tertiary N-alkyl substituents were chlorinated to N-chloro-N-alkoxyamines whose reaction with alcohols enabled synthesis of N,N-dialkoxyamines. The DNMR method was used to determine the barriers of inversion of these compounds. Alkaline hydrolysis (13) followed by subsequent reactions with R-(+)- and S-(?)-α-phenylethylamine yielded diastereomeric salts (+29 and ?29) whose crystallization and subsequent esterification resulted in optically active acyclic amines (?13 and +13) with the asymmetric center only at the N atom in the open chain.