Features and Application in Asymmetric Catalysis of Chiral Phosphine-Phosphite Ligands

被引:11
|
作者
Pizzano, Antonio [1 ,2 ,3 ]
机构
[1] IIQ, Americo Vespucio 49, Seville 41092, Spain
[2] CSIC, Ctr Innovac Quim Avanzada ORFEO CINQA, Americo Vespucio 49, Seville 41092, Spain
[3] Univ Seville, Americo Vespucio 49, Seville 41092, Spain
来源
CHEMICAL RECORD | 2016年 / 16卷 / 06期
关键词
asymmetric catalysis; chirality; enantioselectivity; P ligands; structure-activity relationships; HIGHLY ENANTIOSELECTIVE HYDROGENATION; P-OP LIGANDS; MIXED PHOSPHORUS/SULFUR LIGANDS; ALLYLIC ALKYLATION; GRIGNARD-REAGENTS; PHOSPHINE-PHOSPHITE-RH(I) COMPLEXES; IRIDIUM(I) COMPLEXES; CARBON-MONOXIDE; ALPHA-HYDROXY; ENOL ESTERS;
D O I
10.1002/tcr.201600076
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Chiral phosphine-phosphites are a class of ligands for asymmetric catalysis characterized by two coordinating functionalities with different electronic properties. These ligands also possess a highly modular structure and, due to versatile synthetic processes, they can be tuned precisely in the catalyst optimization process. Research regarding the application of these ligands in several enantioselective catalytic processes has provided outstanding results in a good number of them. These processes include not only Rh catalyzed reactions, such as olefin hydrogenation and hydroformylation, but also other reactions, such as hydrogenation of olefins and imines by Ru complexes, of imines and N-heterocycles by Ir derivatives, allyl alkylation or conjugate addition by Cu catalysts, or hydrocyanation of olefins by Ni ones. Overall, the use of these ligands has led to the preparation of a wide variety of chiral building blocks with high enantiomeric excess. Therefore, phosphine-phosphites have become in an important class of ligands in asymmetric catalysis.
引用
收藏
页码:2599 / 2622
页数:24
相关论文
共 50 条
  • [1] Phosphine-Phosphinite and Phosphine-Phosphite Ligands: Preparation and Applications in Asymmetric Catalysis
    Fernandez-Perez, Hector
    Etayo, Pablo
    Panossian, Armen
    Vidal-Ferran, Anton
    CHEMICAL REVIEWS, 2011, 111 (03) : 2119 - 2176
  • [2] Asymmetric hydroformylation of olefins with Rh catalysts modified with chiral phosphine-phosphite ligands
    Rubio, Miguel
    Suarez, Andres
    Alvarez, Eleuterio
    Bianchini, Claudio
    Oberhauser, Werner
    Peruzzini, Maurizio
    Pizzano, Antonio
    ORGANOMETALLICS, 2007, 26 (25) : 6428 - 6436
  • [3] Asymmetric Hydroformylation Using Taddol-Based Chiral Phosphine-Phosphite Ligands
    Robert, Tobias
    Abiri, Zohar
    Wassenaar, Jeroen
    Sandee, Albertus J.
    Romanski, Steffen
    Neudoerfl, Joerg-Martin
    Schmalz, Hans-Guenther
    Reek, Joost N. H.
    ORGANOMETALLICS, 2010, 29 (02) : 478 - 483
  • [4] A Scalable Synthesis of Chiral Modular Phosphine-Phosphite Ligands
    Dindaroglu, Mehmet
    Falk, Anna
    Schmalz, Hans-Guenther
    SYNTHESIS-STUTTGART, 2013, 45 (04): : 527 - 535
  • [5] Synthesis of P-stereogenic 1-phosphanorbornane-derived phosphine-phosphite ligands and application in asymmetric catalysis
    Ramazanova, Kyzgaldak
    Chakrabortty, Soumyadeep
    Mueller, Bernd H.
    Loennecke, Peter
    de Vries, Johannes G.
    Hey-Hawkins, Evamarie
    RSC ADVANCES, 2023, 13 (49) : 34439 - 34444
  • [6] Chiral phosphine-phosphite ligands in the highly enantioselective rhodium-catalyzed asymmetric hydrogenation
    Deerenberg, S
    Pàmies, O
    Diéguez, M
    Claver, C
    Kamer, PCJ
    van Leeuwen, PWNM
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (23): : 7626 - 7631
  • [7] The synthesis of new chiral phosphine-phosphinites, phosphine-phosphoramidite, and phosphine-phosphite ligands and their applications in asymmetric hydrogenation
    Jia, M
    Li, XS
    Lam, WS
    Kok, SHL
    Xu, LJ
    Lu, G
    Yeung, CH
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2273 - 2278
  • [8] Novel phosphine-phosphite and phosphine-phosphinite ligands for highly enantioselective asymmetric hydrogenation
    Yan, YJ
    Chi, YX
    Zhang, XM
    TETRAHEDRON-ASYMMETRY, 2004, 15 (14) : 2173 - 2175
  • [9] Isostructural Phosphine-Phosphite Ligands in Rhodium-Catalyzed Asymmetric Hydroformylation
    Doro, Franco
    Reek, Joost N. H.
    van Leeuwen, Piet W. N. M.
    ORGANOMETALLICS, 2010, 29 (20) : 4440 - 4447
  • [10] Progress in preparation and application of chiral phosphine ligands in asymmetric catalysis
    Xu, LW
    Xia, CG
    Sun, W
    Li, FW
    Wang, HW
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2003, 23 (09) : 919 - 932