REACTION OF TRIMETHYLSILYLAMINES WITH N-CBZ-L-SERINE-BETA-LACTONE - ACONVENIENT ROUTE TO OPTICALLY PURE BETA-AMINO-L-ALANINE DERIVATIVES

Trimethylsilylamines, Me(3)Si-NR(2), react with N-Cbz-L-serine-beta-la ctone in acetonitrile primarily by alkyl oxygen cleavage of the lacton e ring to give optically pure N-Cbz-beta-amino-L-alanine derivatives i n good yields. Use of halogenate solvents such as chloroform alters th e regiospecificity to give primarily acyl oxygen cleavage and generate amides of N-Cbz-L-serine. The latter are also obtained by reaction of aluminum-amine reagents with the beta-lactone.