ASYMMETRIC SYNTHESIS OF β-LACTAMS. I. THE REACTION OF DIMETHYLKETENE SILYL ACETAL WITH (S)-ALKYLIDENE(1-ARYLETHYL)AMINES PROMOTED BY TITANIUM TETRACHLORIDE

Article abstract of DOI:10.1016/S0040-4039(00)71491-2

Asymmetric synthesis of β-lactams by means of the reaction of dimethyl-ketene silyl acetal with (S)-alkylidene(1-arylethyl)amines in the presence of titanium tetrachloride was studied.The extent of the asymmetric induction was in the range of 44-78percent (diastereomeric purity 72-89percent) and the (S)-configuration was turned to be preferentially induced at the ⁴C position of the resulting β-lactams.