ChemInform Abstract: Triphenylstibine Oxide‐Phosphorus(V) Sulfide as a Novel Condensation Catalyst System: Application to the Synthesis of Dipeptides.

Abstract

Triphenylstibine oxide (Ph3SbO) and phosphorus(V) sulfide (P4S10) synergistically catalyzed the aminolysis of N-protected amino-acids with amino-acid esters in benzene. Ph3SbO accelerated both the initial conversion of carboxylic moieties into the corresponding thiocarboxylic moieties by P4S10 and the subsequent aminolysis of the resulting thiocarboxylic acids. Thus, dipeptides such as Z–A–A′–OEt (where Z = PhCH2OC(O)– and A,A′ = Ala,Gly; Gly,Gly; Leu,Gly; Phe,Gly; Phe,Leu;Ser,Gly; Val,Gly, respectively) were conveniently prepared even at 35°C.