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Triphenylstibine oxide–phosphorus(V) sulfide as a novel condensation catalyst system: application to the synthesis of dipeptides
Author(s) -
Nomura Ryoki,
Yamada Yasuhiro,
Matsuda Haruo
Publication year - 1989
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.590030410
Subject(s) - chemistry , aminolysis , catalysis , sulfide , medicinal chemistry , condensation , benzene , phosphorus , organic chemistry , oxide , condensation reaction , physics , thermodynamics
Triphenylstibine oxide (Ph 3 SbO) and phosphorus(V) sulfide (P 4 S 10 ) synergistically catalyzed the aminolysis of N ‐protected amino‐acids with amino‐acid esters in benzene. Ph 3 SbO accelerated both the initial conversion of carboxylic moieties into the corresponding thiocarboxylic moieties by P 4 S 10 and the subsequent aminolysis of the resulting thiocarboxylic acids. Thus, dipeptides such as Z–A–A′–OEt (where Z = PhCH 2 OC(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.