Asymmetric Synthesis of iso-Boc (S)-2-Amino-8-nonenoic Acid in One Through-Process

A practical through-process to prepare iso-Boc (S)-2-amino-8-nonenoic acid has been developed. The short synthesis utilizes a highly enantioselective, enzymatic reductive amination of an α-keto acid substrate, which is prepared via a Grignard addition to diethyl oxalate. Starting from 7-bromohept-1-ene and without isolation of any intermediates, iso-Boc (S)-2-amino-8-nonenoic acid is prepared in 60% overall yield and >99.9% ee.