Premium
Selective Rhodium‐Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides
Author(s) -
Das Shoubhik,
Li Yuehui,
Bornschein Christoph,
Pisiewicz Sabine,
Kiersch Konstanze,
Michalik Dirk,
Gallou Fabrice,
Junge Kathrin,
Beller Matthias
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201503584
Subject(s) - chemistry , hydrosilylation , rhodium , combinatorial chemistry , amide , catalysis , nitrile , reagent , functional group , derivatization , organic chemistry , reductive amination , ligand (biochemistry) , selectivity , peptide , selective reduction , biochemistry , high performance liquid chromatography , receptor , polymer
Abstract Efficient reduction of the tertiary amide bond in amino acid derivatives and peptides is described. Functional group selectivity has been achieved by applying a commercially available rhodium precursor and bis(diphenylphosphino)propane (dppp) ligand together with phenyl silane as a reductant. This methodology allows for specific reductive derivatization of biologically interesting peptides and offers straightforward access to a variety of novel peptide derivatives for chemical biology studies and potential pharmaceutical applications. The catalytic system tolerates a variety of functional groups including secondary amides, ester, nitrile, thiomethyl, and hydroxy groups. This convenient hydrosilylation reaction proceeds at ambient conditions and is operationally safe because no air‐sensitive reagents or highly reactive metal hydrides are needed.