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Title
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Selective rhodium-catalyzed reduction of tertiary amides in amino acid esters and peptides
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Author
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Abstract
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| 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. |
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Language
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English
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Source (journal)
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Angewandte Chemie: international edition in English. - Weinheim
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Publication
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Weinheim
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2015
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ISSN
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1433-7851
0570-0833
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DOI
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10.1002/ANIE.201503584
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Volume/pages
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54
:42
(2015)
, p. 12389-12393
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ISI
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000363397300024
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Full text (Publisher's DOI)
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