A METHOD FOR THE SYNTHESIS OF ALKYNYL PHENYL SULFIDES FROM ALKYNYLTRIMETHYLSILANES - A NOVEL, EFFICIENT SYNTHESIS OF THE THIENAMYCIN INTERMEDIATE FROM 3(R)-HYDROXYBUTYRIC ACID

The mechanism of the one-pot conversion of /3-amino thiol esters of type 3 to /3-lactams of type 4 has been clarified, and it is proposed that the actual active species is a PhSSPh-CuOTf complex. Through the use of this novel reaction, an efficient synthesis of the thienamycin intermediate 2, starting with 3(i?)-hydroxybutyric acid, has been achieved. Furthermore, the combined reagents (PhSSPh-CuOTf) have been demonstrated to be a powerful source of PhS+ through the conversion of several alkynyltrimethylsilanes to alkynyl phenyl sulfides. © 1990, American Chemical Society. All rights reserved.