21156-62-7Relevant articles and documents
P-Chirogenic Triazole-Based Phosphine: Synthesis, Coordination Chemistry, and Asymmetric Catalysis
Bayardon, Jér?me,Rousselle, Benjamin,Rousselin, Yoann,Bonnin, Quentin,Malacea-Kabbara, Raluca
, p. 4723 - 4729 (2020)
Herein we report the synthesis of a new P-chirogenic triazole-based phosphine according to the ephedrine methodology. Upon reaction with late transition-metal derivatives, RhI and PdII, phosphine-triazole forms complexes with bidenta
Extensive re-investigations of pressure effects in rhodium-catalyzed asymmetric hydrogenations
Alame, Mohamad,Pestre, Nathalie,De Bellefona, Claude
, p. 898 - 908 (2008)
The catalytic hydrogenation of three prochiral substrates methyl Z-α-acetamidocinnamate (MAC), methyl 2-acetamidoacrylate (M-Acrylate) and ethyl 4-methyl-3-acetamido-2-propanoate (EEMAP) with rhodium precursors complexed with chiral diphosphines is report
Phosphorus-Chiral Analogues of 1,1′-Bis(diphenylphosphino)ferrocene: Asymmetric Synthesis and Application in Highly Enantioselective Rhodium-Catalyzed Hydrogenation Reactions
Nettekoven, Ulrike,Kamer, Paul C.J.,Van Leeuwen, Piet W.N.M.,Widhalm, Michael,Spek, Anthony L.,Lutz, Martin
, p. 3996 - 4004 (1999)
Five new ferrocene ligands 1a-e (1 = 1,1′-bis(aryl-phenylphosphino)ferrocene with aryl residues a = 1-naphthyl, b = 2-naphthyl, c = 2-anisyl, d = 2-biphenylyl, and e = 9-phenanthryl) bearing stereogenic phosphorus atoms have been prepared in enantiomerica
Evidence for the importance of conformational equilibria in Rh-diphosphine complexes for the enantioselection in Rh-catalyzed asymmetric hydrogenation
Tsuruta, Hideyuki,Imamoto, Tsuneo,Yamaguchi, Kentaro,Gridnev, Ilya D.
, p. 2879 - 2882 (2005)
The conformations of the chelate cycles in the X-ray structures of norbornadiene- and cyclooctadiene-rhodium complexes of (R,R)-1,2-bis[(o- methylphenyl)phenylphosphino]ethane are dramatically different. Nevertheless, they demonstrate the same sense of enantioselection in asymmetric hydrogenation of dehydroamino acids.
Synthesis of (-)-(4R,5R)-4,5-bis[di-3',(2',6'- dimethoxypyridyl)phosphinomethyl]-2,2-dimethyl-1,3-dioxolane and its application in the Rh-catalyzed asymmetric hydrogenation reactions
Hu, Wenhao,Chen, Chih-Chiang,Xue, Guoping,Chan, Albert S. C.
, p. 4183 - 4192 (1998)
The chiral ligand (-)-(4R,5R)-4,5-bis[di-3'-(2',6'- dimethoxypyridyl)phosphinomethyl]-2,2-dimethyl-1,3-dioxolane 3 [(R,R)-Py*- DIOP] was synthesized via a key intermediate bis[3-(2,6- dimethoxypyridyl)]phosphineborane 9. The asymmetric hydrogenation of pr
Further insight in the minor/major concept using hydrogen pressure effect in asymmetric hydrogenation
Aloui, A.,De Bellefon, C.,Delbecq, F.,Sautet, P.
, p. 214 - 222,9 (2012)
The catalytic system prepared from [Rh(COD)2]BF4 and (R,R)-Me-BPE provides a spectacular detrimental hydrogen pressure effect on ee from 94% down to 56% in the hydrogenation of methylacrylate, whereas it has a strong beneficial effect on the hydrogenation of E-emap (from 42% up to 72%). The kinetic parameters have been determined for both systems and have helped to identify the most enantioselective controlling steps (MECS). Accordingly, further explanations for the structure-ee and hydrogen pressure relationship are proposed.
Influence of different types of amphiphiles on the rhodium(I) complex-catalyzed asymmetric hydrogenation of (Z)-methyl-α-acetamidocinnamate in aqueous medium
Grassert,Paetzold,Oehme
, p. 6605 - 6612 (1993)
The homogeneous asymmetric hydrogenation of (Z)-methyl-α-acetamidocinnamate catalyzed by the system [Rh(COD)2]BF4 + 1.1 BPPM could be effected in water as medium in the presence of micelle-forming amphiphiles. Both activity and enant
Hydrophosphination of Bicyclo[1.1.0]butane-1-carbonitriles
Milligan, John A.,Busacca, Carl A.,Senanayake, Chris H.,Wipf, Peter
, p. 4300 - 4303 (2016)
Hydrophosphination of bicyclo[1.1.0]butyl nitriles with phosphine boranes and phosphites provided novel cyclobutyl-P derivatives. The reaction generally favors the syn-diastereomer, and the nitrile can be reduced and converted to other functional groups, thus enabling the preparation of bidentate ligands that access new conformational space by virtue of their attachment to the torsionally malleable but sterically restrictive cyclobutane scaffold. The enantioselective hydrogenation of dehydrophenylalanine using a bidentate phosphine-phosphite ligand illustrates the synthetic utility of the newly prepared scaffold.
A one-step, modular route to optically-active diphos ligands
Louise Hazeland,Chapman, Andy M.,Pringle, Paul G.,Sparkes, Hazel A.
, p. 10206 - 10209 (2015)
A chlorosilane elimination reaction has been developed that allows the efficient synthesis of optically pure C1-symmetric, C1-backboned diphosphines with a wide variety of stereoelectronic characteristics.
Synthesis of a new bulky phosphite ligand and its application in the enantioselective hydrogenation
Sokolovskaya, Marina V.,Lyubimov, Sergey E.,Mikhel, Igor S.,Birin, Kirill P.,Davankov, Vadim A.
, p. 230 - 233 (2018)
A new bulky phosphite ligand was synthesized and tested in the asymmetric Rh-catalyzed hydrogenation of a series of substrates, including dimethyl itaconate (up to 95% ee), α- and β-dehydroamino acid derivatives (up to 88% and 76% ee, respectively). In th
