ASYMMETRIC SYNTHESIS OF β-LACTAMS BY CHIRAL ESTER ENOLATE-IMINE CONDENSATION

Article abstract of DOI:10.1016/S0040-4039(00)97603-2

Asymmetric cyclocondensation of N,N-bis(silyl)glycinates bearing chiral ester moieties with aldimines is found to proceed with extremely high enantioselectivity to give the corresponding chiral β-lactams in good to high yields.It is found that the E/Z-geometry of the chiral ester-enolate is responsible for cis/trans stereochemistry of the β-lactam formed.Effects of various chiral auxiliaries in the ester-enolates on the enantioselectivity of the reactions are examined.