6436-91-5Relevant academic research and scientific papers
Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides
Das, Shoubhik,Li, Yuehui,Bornschein, Christoph,Pisiewicz, Sabine,Kiersch, Konstanze,Michalik, Dirk,Gallou, Fabrice,Junge, Kathrin,Beller, Matthias
supporting information, p. 12389 - 12393 (2015/10/12)
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.
