Triphenylstibine oxide–phosphorus(V) sulfide as a novel condensation catalyst system: application to the synthesis of dipeptides | Zendy

Nomura Ryoki | Zendy; Yamada Yasuhiro | Zendy; Matsuda Haruo | Zendy

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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.

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