SYNTHESIS OF DIASTEREO- AND ENANTIOMERICALLY PURE α-AMINO-γ-OXO ACID ESTERS BY REACTION OF ACYLIMINOACETATES WITH ENAMINES DERIVED FROM 6-MEMBERED KETONES

Article abstract of DOI:10.1016/S0040-4020(01)96483-X

A new efficient diastereo- and enantioselective synthesis of α-amino-γ-oxo acid esters by reaction of acyliminoacetates with enamines is described.By employing the concept of double stereodifferentiation, complete asymmetric induction (de=ee >/= 99.9 percent) for the C-C bond formation is obtained.Desulphurization of a sulphur containing product leads to the corresponding acyclic amino acid derivatives.The virtually complete anti-diastereo- and enantioselectivities are interpreted by a Diels-Alder like transition state.