Complete stereoselective synthesis of chiral intermediates for thienamycin and related antibiotics

The complete stereoselective synthesis of (3R,4R)-3-[(S)-1′-hydroxyethyl]-4-phenylethynyl-2-azetidinone and its 4-phenyethenyl derivative were accomplished by the reaction of the organozinc derivative of (R)-methyl-3-hydroxybutyrate with N-trimethylsilylimines.