69390-41-6Relevant academic research and scientific papers
Practical syntheses of N-acetyl (E)-β-arylenamides
Cai, Zhihua,Liu, Guodu,Jiao, Guangjun,Senanayake, Chris H.,Tang, Wenjun
, p. 3355 - 3360 (2014/01/06)
A facile and practical method for the preparation of (E)-β- arylenamides [(E)-N-(1-arylprop-1-en-2-yl]acetamides] has been developed by reductive acetylation of the corresponding oximes with iron(II) acetate as the reducing reagent. Employment of hexamethylphosphoramide as the solvent was found to be critical for the high E/Z selectivity. The methodology has been applied in efficient syntheses of a key chiral intermediate of tamsulosin by asymmetric hydrogenation. Georg Thieme Verlag Stuttgart . New York.
Design of phosphorus ligands with deep chiral pockets: Practical Synthesis of chiral β-arylamines by asymmetric hydrogenation
Liu, Guodu,Liu, Xiangqian,Cai, Zhihua,Jiao, Guangjun,Xu, Guangqing,Tang, Wenjun
, p. 4235 - 4238 (2013/05/08)
WingPhos, a C2-symmetric bisphosphorus ligand with a deep and well-defined chiral pocket was developed. It has shown high efficiency in the rhodium-catalyzed asymmetric hydrogenation of (E)-β-aryl-N-acetyl enamides, cyclic β-aryl enamides, and heterocyclic β-aryl enamides. A series of chiral β-arylisopropylamines, 2-aminotetralines, and 3-aminochromans can be synthesized with excellent ee values (nbd=3,5-norbornadiene; TON=turnover number). Copyright
Enantioselective hydrogenation of (Z)- and (E)-β-arylenamides catalyzed by rhodium complexes of monodentate chiral spiro phosphorous ligands: A new access to chiral β-arylisopropylamines
Zhu, Shou-Fei,Liu, Tao,Yang, Shuang,Song, Song,Zhou, Qi-Lin
supporting information; experimental part, p. 7685 - 7690 (2012/09/07)
A highly enantioselective rhodium-catalyzed hydrogenation of both (Z)- and (E)-β-arylenamides was developed by using monodentate chiral spiro phosphite and phosphine ligands, respectively. The hydrogenation reaction provides an efficient access to optically active β-arylisopropylamines, important building blocks for the synthesis of biologically active compounds.
Efficient synthesis of chiral β-arylisopropylamines by using catalytic asymmetric hydrogenation
Chen, Jian,Zhang, Weicheng,Geng, Huiling,Li, Wei,Hou, Guohua,Lei, Aiwen,Zhang, Xumu
supporting information; experimental part, p. 800 - 802 (2009/05/06)
(Chemical Equation Presented) Direct condensation of β-arylketones with acetamide afforded both Z and E enamides. The Z-configured substrates underwent hydrogenation with excellent enantioselectivity by using the Rh/tang-phos catalytic system (see scheme; tangphos = 1,1′-di-tert-butyl- [2,2′]-diphospholanyl). The product β-arylisopropylamines are important precursors to several drugs.
A new selective reduction of nitroalkenes into enamides
Laso, Nieves M.,Quiclet-Sire, Beatrice,Zard, Samir Z.
, p. 1605 - 1608 (2007/10/03)
Conjugated nitroalkenes can be reduced into enamides by a combination of iron powder, a carboxylic acid, and the corresponding anhydride.
