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
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.