Reaction of a serine-derived organozinc reagent with chloroformates and ethyl oxalyl chloride under palladium catalysis. Preparation of protected (2S, 6S)-4-oxo-2,6-diaminopimelic acid and (2S)-4-oxoglutamic acid

Abstract

Organozinc reagent 1 reacts with phenyl chloroformate under palladium catalysis to give the protected 4-oxo-2,6-diaminopimelic acid derivative 3, derived by formal displacement of both chloride and phenoxide; the symmetrical ketone 3, together with protected 4-oxoglutamic acid 10, are formed when ethyl oxalyl chloride is used as substrate.