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
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
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
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
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.
Enantiomerically pure 1,2,5-triphenylphospholane through the synthesis and resolution of the chiral trans-(2,5)-diphenylphospholanic acid
Guillen, Frederic,Fiaud, Jean-Claude
, p. 2939 - 2942 (1999)
The synthesis and resolution of trans-(2,5)-diphenylphospholanic acid 7 is described. The phosphinic acid 7 was converted into optically active (1,2,5)-triphenylphospholane 5 which was used as a chiral ligand in Rh- catalyzed hydrogenation of N-acetyl deh
Parallel synthesis and screening of polymer-supported phosphorus- stereogenic aminophosphane-phosphite and -phosphinite ligands
Den Heeten, Rene,Swennenhuis, Bert H. G.,Van Leeuwen, Piet W. N. M.,De Vries, Johannes G.,Kamer, Paul C. J.
, p. 6602 - 6605 (2008)
(Chemical Equation Presented) Bound to Ps: An efficient, rapid, parallel solid-phase synthesis of a series of resin-bound P-stereogenic aminophosphane-phosphinite and -phosphite ligands is developed (see scheme).The ligands form active hydrogenation catal
HYDROGENATION OF DEHYDROAMINO ACIDS IN THE PRESENCE OF PALLADIUM(II) COMPLEXES WITH METHIONINE
Lisichkina, I. N.,Vinogradova, A. I.,Saporovskaya, M. B.,Latov, V. K.,Velikov, V. M.
, p. 1029 - 1031 (1988)
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CATALYTIC ASYMMETRIC SYNTHESIS OF METHYL ESTER OF N-ACETYL-α-PHENYLALANINE ON CHIRAL COBALT COMPLEXES
Nindakova, L. O.,Shmidt, F. K.,Klabunovskii, E. I.,Pavlov, V. A.
, p. 671 - 673 (1984)
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Rhodium/olefin-catalyzed reaction of arylboronic acids with an α-acetamido acrylic ester: Mizoroki-Heck-type reaction versus asymmetric conjugate addition
Noel, Timothy,Goek, Yasar,Eycken, Johan Van der
, p. 540 - 543 (2010)
In this paper we present our results concerning the rhodium/olefin-catalyzed reaction of arylboronic acids with an α-acetamido acrylic ester. With a chiral norbornadiene ligand rather low enantioselectivities (up to 21% ee) were obtained. Besides the expected conjugate adduct, we also observed the formation of a significant amount of Mizoroki-Heck-type product. The ratio of the conjugate adduct/Mizoroki-Heck product could be adjusted by a proper choice of the olefin ligand.
Interception and Characterization of a Hydridialkylrhodium Intermediate in a Homogeneous Catalytic Hydrogenation Reaction
Chan, A. S. C.,Halpern, Jack
, p. 838 - 840 (1980)
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Mixtures of ionic liquids and water as a medium for efficient enantioselective hydrogenation and catalyst recycling
Pugin,Studer,Kuesters,Sedelmeier,Feng
, p. 1481 - 1486 (2004)
In a screening of ligands, ionic liquids and reaction conditions in the Rh-catalyzed hydrogenation of enamides, a novel multi-phase reaction system consisting of an ionic liquid (IL) and water (wet ILs) was found to give the most promising results. In many cases such IL/water combinations were superior compared to conventional organic solvents and biphasic ILs/organic co-solvents media with respect to catalytic performance as well as to catalyst separation and recycling. So far, the best results were obtained with Rh-ferrocenyl- diphosphine catalysts (>99% ee). Generally, somewhat lower ees were observed at higher pressure. However, this effect was less pronounced with wet ILs than with conventional solvents. It is shown that IL/water combination allow repeated catalyst recycling without significant loss of activity and that industrially relevant turnover numbers of > 10,000 can be obtained.
Rapid Synthesis of Chiral 1,2-Bisphosphine Derivatives through Copper(I)-Catalyzed Asymmetric Conjugate Hydrophosphination
Xiao, Jun-Zhao,Yin, Liang,Yue, Wen-Jun,Zhang, Shuai
, p. 7057 - 7062 (2020)
1,2-Bisphosphines have been identified as one class of important and powerful chiral ligands in asymmetric catalysis with transition metals. Herein, a copper(I)-catalyzed asymmetric hydrophosphination of α,β-unsaturated phosphine sulfides was developed wi
A novel approach for investigating enantioselectivity in asymmetric hydrogenation
Shimizu, Hideo,Ishizaki, Takero,Fujiwara, Takahiro,Saito, Takao
, p. 2169 - 2172 (2004)
A new and convenient method for investigating the relationship between the position of the enantiodetermining sites in chiral phosphine ligands and enantioselectivity in asymmetric hydrogenation is proposed. We have also synthesized four new diphosphine l
Chiral polycyclic tropane compound as well as preparation method and application thereof
-
, (2021/08/25)
The invention provides a chiral polycyclic tropane compound as well as a preparation method and application thereof. The invention specifically relates to a tropane compound shown as a formula I, or a salt thereof, or a stereoisomer thereof, or a crystal form thereof, and a preparation method and application thereof. The preparation method disclosed by the invention is simple in process, mild in reaction condition and high in yield, and the obtained product has excellent enantioselectivity and diastereoselectivity. Experiments prove that the tropane compound can effectively inhibit various tumor cells, especially lung cancer cells, melanoma cells, breast cancer cells, in-situ pancreatic cancer cells and pancreatic cancer cells, so that the compound has a wide prospect in preparation of drugs for preventing and/or treating tumors.
Asymmetric Full Saturation of Vinylarenes with Cooperative Homogeneous and Heterogeneous Rhodium Catalysis
Andersson, Pher G.,Massaro, Luca,Peters, Bram B. C.,Wu, Haibo,Yang, Jianping,Zheng, Jia
supporting information, p. 20377 - 20383 (2021/12/03)
Homogeneous and heterogeneous catalyzed reactions can seldom operate synergistically under the same conditions. Here we communicate the use of a single rhodium precursor that acts in both the homogeneous and heterogeneous phases for the asymmetric full saturation of vinylarenes that, to date, constitute an unmet bottleneck in the field. A simple asymmetric hydrogenation of a styrenic olefin, enabled by a ligand accelerated effect, accounted for the facial selectivity in the consecutive arene hydrogenation. Tuning the ratio between the phosphine ligand and the rhodium precursor controlled the formation of homogeneous and heterogeneous catalytic species that operate without interference from each other. The system is flexible in terms of both the chiral ligand and the nature of the external olefin. We anticipate that our findings will promote the development of asymmetric arene hydrogenations.
