CHEMISTRY OF O-SILYLATED KETENE ACETALS - A STEREOSELECTIVE SYNTHESIS OF OPTICALLY-ACTIVE CARBAPENEM ANTIBIOTICS, (+)-THIENAMYCIN AND (+)-PS-5

A stereoselective synthesis of the chiral thienamycin intermediate (16) involving a diastereoselective Micheal addition and a silicon-induced Pummerer-type reaction is described. In a similar way, the key intermediate for (+)-PS-5 was also prepared from 4-(phenylsulfinylmethyl)butanamide (21).