Selective Rhodium‐Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides

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 m...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie 2015-10, Vol.127 (42), p.12566-12570
Main Authors: Das, Shoubhik, Li, Yuehui, Bornschein, Christoph, Pisiewicz, Sabine, Kiersch, Konstanze, Michalik, Dirk, Gallou, Fabrice, Junge, Kathrin, Beller, Matthias
Format: Article
Language:English
Subjects:
Amidbindung
Amides
Amino acids
Aminosäure
Chemistry
Derivatives
Esters
Functional groups
Hydrosilylation
Peptides
Peptidmodifikation
Phenyls
Reduction
Rhodium
Selektive Reduktion
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Modifikation von Peptiden: Die Verwendung eines handelsüblichen Rhodiumkomplexes mit dem Bis(diphenylphosphan)propan(dppp)‐Liganden und Phenylsilan als Reduktionsmittel ermöglicht die spezifische reduktive Derivatisierung von biologisch interessanten Peptiden.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201503584