1. Selective rhodium-catalyzed reduction of tertiary amides in amino acid esters and peptides.
- Author
-
Das S, Li Y, Bornschein C, Pisiewicz S, Kiersch K, Michalik D, Gallou F, Junge K, and Beller M
- Subjects
- Catalysis, Molecular Structure, Oxidation-Reduction, Amides chemistry, Amino Acids chemistry, Esters chemistry, Organometallic Compounds chemistry, Peptides chemistry, Rhodium chemistry
- 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., (© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
- Published
- 2015
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