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Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides†
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This work is supported by the state of Mecklenburg-Vorpommern and the BMBF (Bundesministerium für Bildung und Forschung). We thank Novartis Pharma AG for funding and Dr. Florian Rampf (Novartis Pharma AG) for his support.
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.