83528-04-5Relevant articles and documents
BF3·Et2O as a metal-free catalyst for direct reductive amination of aldehydes with amines using formic acid as a reductant
Fan, Qing-Hua,Liu, Xintong,Luo, Zhenli,Pan, Yixiao,Xu, Lijin,Yang, Ji,Yao, Zhen,Zhang, Xin
supporting information, p. 5205 - 5211 (2021/07/29)
A versatile metal- and base-free direct reductive amination of aldehydes with amines using formic acid as a reductant under the catalysis of inexpensive BF3·Et2O has been developed. A wide range of primary and secondary amines and diversely substituted aldehydes are compatible with this transformation, allowing facile access to various secondary and tertiary amines in high yields with wide functional group tolerance. Moreover, the method is convenient for the late-stage functionalization of bioactive compounds and preparation of commercialized drug molecules and biologically relevant N-heterocycles. The procedure has the advantages of simple operation and workup and easy scale-up, and does not require dry conditions, an inert atmosphere or a water scavenger. Mechanistic studies reveal the involvement of imine activation by BF3and hydride transfer from formic acid.
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 (2015/10/12)
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.
The First Enantioselectice Total Syntheses of the Allopumiliotoxin A Alkaloids 267A and 339B
Goldstein, Steven W.,Overmann, Larry E.,Rabinowitz, Michael H.
, p. 1179 - 1190 (2007/10/02)
Short, highly stereocontrolled, asymmetric total syntheses of the title amphibian alkaloids are described.In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form.This short sequence proceeds in five laborato
