92010-20-3Relevant articles and documents
Selective Rhodium-Catalyzed Reduction of Tertiary Amides in Amino Acid Esters and Peptides
Das, Shoubhik,Li, Yuehui,Bornschein, Christoph,Pisiewicz, Sabine,Kiersch, Konstanze,Michalik, Dirk,Gallou, Fabrice,Junge, Kathrin,Beller, Matthias
supporting information, p. 12389 - 12393 (2015/10/12)
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.
Efficient one-pot formation of amides from benzyl carbamates: Application to solid-phase synthesis
Li, Wen-Ren,Yo, Ying-Chih,Lin, Yu-Sheng
, p. 8867 - 8875 (2007/10/03)
A convenient one-pot protocol for the conversion of benzyl carbamates to amides is described. The general applicability of the procedure is illustrated using various types of substrates. This new method proceeds rapidly under mild conditions, in good yields, and without noticeable racemization. This protocol was applied to solid-phase synthesis to prepare amides and esters from Merrifield resin-bound carbamates and carbonates. (C) 2000 Elsevier Science Ltd.
Electronic effect of prolinate ligand-dirhodium(ii) complexes on catalytic asymmetric dipolar cycloaddition
Ishitani, Hitoshi,Achiwa, Kazuo
, p. 153 - 156 (2007/10/03)
We prepared several efficient chiral N-benzoylpyrroridinecarboxylic acid ligands for dirhodium-catalyzed asymmetric dipolar cycloaddition and found that the electronic effect of the dirhodium(II) complexes influenced the catalytic activity, and the electr