610758-06-0Relevant articles and documents
Enantioselective copper(II)-catalyzed Henry reaction utilizing chiral aziridinyl alcohols
Wang, Xiaojuan,Zhao, Wenxian,Li, Gaowei,Wang, Jin,Liu, Guanjun,Liu, Lantao,Zhao, Ruijuan,Wang, Mincan
, p. 892 - 899 (2014)
A family of enantiopure β-aminoalcohols based on aziridine backbones were synthesized, and examined as chiral ligands for the copper(II)-catalyzed asymmetric Henry reaction of aromatic aldehydes with nitromethane, giving β-nitroalcohols in excellent yield
Henry reaction catalyzed by new series of imidazolidine-4-one Cu-complexes
Drabina, Pavel,Horáková, Eva,R??i?ková, Zdeňka,Sedlák, Milo?
, p. 141 - 147 (2015)
A series of 5-tert-butyl-2-(pyridine-2-yl)imidazolidine-4-ones have been prepared and their Cu(II) complexes studied as enantioselective catalysts of the asymmetric Henry reaction of various aldehydes with nitromethane. It was found that these compounds w
(3S,4S)-N-substituted-3,4-dihydroxypyrrolidines as ligands for the enantioselective Henry reaction
Rénio, Márcia R.R.,Sousa, Francisco J.P.M.,Tavares, Nélia C.T.,Valente, Artur J.M.,da Silva Serra, M. Elisa,Murtinho, Dina
, (2021/02/03)
The enantioselective Henry reaction is a very important and useful carbon–carbon bond forming reaction. The execution of this reaction requires the use of efficient chiral catalysts. In this work, in situ formed complexes of N-substituted dihydroxypyrrolidines, chiral ligands derived from L-tartaric acid and amines, were evaluated as catalysts in the enantioselective Henry reaction. The results showed that the nature of the N-substituent on the ligand significantly influences the outcome of the reaction. Best results were obtained using a Cu (II) complex of (3S,4S)-N-benzyl-3,4-dihydroxypyrrolidine, in the presence of DIPEA, for the reaction of aromatic aldehydes with nitromethane, at room temperature, originating products with er up to 92:8 (R:S) and conversions up to 96%. The interaction between the pyrrolidine ligand and the copper ion, in isopropanol, was followed by UV-vis spectrophotometry, showing a 1:1 stoichiometry and a binding constant of 4.4. The results obtained will contribute to the design and development of more efficient chiral catalysts for this type of reaction.
Asymmetric Cu-catalyzed Henry reaction using chiral camphor Schiff bases immobilized on a macromolecular chain
Zhang, Kaihua,Sun, Jialin,Xu, Jingwen,Li, Gaoqiang,Xu, Feng
, p. 1819 - 1824 (2019/06/18)
Immobilized catalysts have attracted chemists’ attention for long time because of convenient recycling, which is very important for some special catalyst even immobilizations accompanying the decrease of catalytic activity and selectivity. Our group focus
Isosteric expansion of the structural diversity of chiral ligands: Design and application of proline-based N,N′-dioxide ligands for copper-catalyzed enantioselective Henry reactions
Gao, En,Li, Meng,Duan, Lili,Li, Lin,Li, Yue-Ming
supporting information, (2019/08/16)
Chiral N,N′-dioxide catalysts were designed based on isosteric approach. Using L-Proline as the starting material, a variety of chiral N,N′-dioxide ligands were obtained via conventional functional group transformations and were utilized in asymmetric Henry reactions between nitromethane and aromatic aldehydes. Using the N,N′-dioxide-copper(II) complexes as the catalysts, asymmetric Henry reaction produced the corresponding β-nitroalcohols in up to 66% yields and up to 83% ee's under mild conditions. The reactions were easy to carry out, and special care such as air or moisture-free conditions was not required.
