Synthesis of bis(α-amino acids) by palladium-catalyzed allylic double substitution

Abstract

The reaction of lithium enolate derived from benzophenone imine of glycine ethyl ester 1 with allylic dihalides 2 in the presence of a catalytic amount of Pd(Ph3)4 (5% mol) affords the corresponding bis(imino esters) 3. Subsequent hydrolysis of compounds 3 gives the corresponding bis (α-amino acids) 4. This methododology has been used to synthesise α,α’-diaminosuberic acid.