N-(Boc)-L-(2-Bromoallyl)-glycine: A versatile intermediate for the synthesis of optically active unnatural amino acids

Abstract

N(Boc)-L-(2-Bromoallyl)-glycine (1) was synthesized from diethylacetamidomalonate and 2,3-dibromopropene in a one-pot procedure (75 % overall yield). The enantiomers were efficiently separated via a tandem biocatalytic kinetic hydrolytic resolution. 1 was elaborated to several other interesting unnatural amino acid. © 1993.