100618-39-1Relevant academic research and scientific papers
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
, p. 12389 - 12393 (2015)
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.
Direct catalytic N-alkylation of amines with carboxylic acids
Sorribes, Iván,Junge, Kathrin,Beller, Matthias
, p. 14314 - 14319 (2014/12/10)
A straightforward process for the N-alkylation of amines has been developed applying readily available carboxylic acids and silanes as the hydride source. Complementary to known reductive aminations, effective C-N bond construction proceeds under mild conditions and allows obtaining a broad range of alkylated secondary and tertiary amines, including fluoroalkyl-substituted anilines as well as the bioactive compound Cinacalcet HCl.
Selective reduction of amides to amines by boronic acid catalyzed hydrosilylation
Li, Yuehui,Molina De La Torre, Jesus A.,Grabow, Kathleen,Bentrup, Ursula,Junge, Kathrin,Zhou, Shaolin,Brueckner, Angelika,Beller, Matthias
, p. 11577 - 11580 (2013/11/06)
Not a 'B'ore! Benzothiophene-based boronic acids catalyze the reduction of tertiary, secondary, and primary amides in the presence of a hydrosilane. The reaction demonstrates good functional-group tolerance. Copyright
A Study of Electronic Effects Involving Electron Deficient Nitrogen : Part IV - Schmidt & Beckmann Rearrangements of Isoquinolinones & Isothiachromanone
Venugopal, V. K.,Rao, Nagabhushan,Rahman, M. F.,Bhalerao, U. T.
, p. 156 - 157 (2007/10/02)
Schmidt and Beckmann rearrangements of isoquinolinones (1,2) and isothiachromanone (3) afford exclusively seven-membered lactams (4,5,6) resulting from aryl bond migration.No alkyl bond migration is observed as in chromanones.
