Stereocontrolled synthesis of (+)-thienamycin from 3(R)-hydroxybutyric acid

Article abstract of DOI:10.1016/S0040-4039(00)98542-3

The vinyloxyborane(5), prepared from (+)-S-phenyl-3(R)-butanethioate, 9-BBN triflate and diisopropylethylamine, reacted with N-(3-benzyloxypropylidene)benzylamine to give the β-benzylamino thiol ester(6) in a moderate yield, which was efficiently converted to the optically pure thienamycin intermediate(10).