title: Selective rhodium-catalyzed reduction of tertiary amides in amino acid esters and peptides.
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.
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Shoubhik
authors.initials: S
authors.lastname: Das
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Yuehui
authors.initials: Y
authors.lastname: Li
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Christoph
authors.initials: C
authors.lastname: Bornschein
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Sabine
authors.initials: S
authors.lastname: Pisiewicz
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Konstanze
authors.initials: K
authors.lastname: Kiersch
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Dirk
authors.initials: D
authors.lastname: Michalik
authors.affiliation: Novartis Pharma AG, 4002 Basel (Switzerland).
authors.forename: Fabrice
authors.initials: F
authors.lastname: Gallou
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de.
authors.forename: Kathrin
authors.initials: K
authors.lastname: Junge
authors.affiliation: Leibniz-Institut für Katalyse e.V. Albert-Einstein-Str. 29a, 18059 Rostock (Germany) http://www.catalysis.de. matthias.beller@catalysis.de.
authors.forename: Matthias
authors.initials: M
authors.lastname: Beller
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D010455:Peptides / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*
chemical_list: D000577:Amides; D000596:Amino Acids; D004952:Esters; D009942:Organometallic Compounds; D010455:Peptides; D012238:Rhodium
keywords: amide bond; amino acid; peptide modification; rhodium; selective reduction