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

Title data

Das, Shoubhik ; Li, Yuehui ; Bornschein, Christoph ; Pisiewicz, Sabine ; Kiersch, Konstanze ; Michalik, Dirk ; Gallou, Fabrice ; Junge, Kathrin ; Beller, Matthias:
Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides.
In: Angewandte Chemie International Edition. Vol. 54 (2015) Issue 42 . - pp. 12389-12393.
ISSN 1521-3773
DOI: https://doi.org/10.1002/anie.201503584

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I > Chair Organic Chemistry I - Univ.-Prof. Dr. Das Shoubhik
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Chemistry > Chair Organic Chemistry I
Result of work at the UBT: No
DDC Subjects: 500 Science > 540 Chemistry
Date Deposited: 20 Jul 2023 09:22
Last Modified: 08 Nov 2023 11:23
URI: https://eref.uni-bayreuth.de/id/eprint/86220