Reaction of trimethylsilylamines with N-Cbz-l-serine-β-lactone: A convenient route to optically pure β-amino-l-alanine derivatives

ES Ratemi, JC Vederas

Index: Ratemi, Elaref S.; Vederas, John C. Tetrahedron Letters, 1994 , vol. 35, # 41 p. 7605 - 7608

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Citation Number: 34

Abstract

Abstract Trimethylsilylamines, Me 3 Si-NR 2, react with N-Cbz-L-serine-β-lactone in acetonitrile primarily by alkyl oxygen cleavage of the lactone ring to give optically pure N- Cbz-β-amino-L-alanine derivatives in good yields. Use of halogenated solvents such as chloroform alters the 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 ...