New unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligands derived from H8-BINOL for highly efficient Rh-catalyzed enantioselective hydrogenation

被引:42
|
作者
Zeng, QH
Hu, XP
Duan, ZC
Liang, XM
Zheng, Z [1 ]
机构
[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
[2] Chinese Acad Sci, Grad Sch, Beijing 100039, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetasy.2005.02.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A series of new H-8-BINOL-derived unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligands have been synthesized and successfully used in Rh-catalyzed asymmetric hydrogenations. The same or higher enantioselectivities (99.9% ee) were achieved in the hydrogenation of dimethyl itaconate and alpha-dehydroamino acid esters as those obtained with BINOL-derived analogues. However, slightly lower enantioselectivities (99.0% ee) were obtained in the hydrogenation of enamides. (C) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1233 / 1238
页数:6
相关论文
共 16 条
  • [1] Monophosphite ligands derived from carbohydrates and H8-BINOL:: highly enantioselective Rh-catalyzed asymmetric hydrogenations
    Huang, HM
    Liu, XC
    Chen, HL
    Zheng, Z
    TETRAHEDRON-ASYMMETRY, 2005, 16 (03) : 693 - 697
  • [2] Highly enantioselective hydrogenation of enamides catalyzed by rhodium-monodentate phosphoramidite complex derived from H8-BINOL
    Li, XS
    Jia, X
    Lu, G
    Au-Yeung, TTL
    Lam, KH
    Lo, TWH
    Chan, ASC
    TETRAHEDRON-ASYMMETRY, 2003, 14 (18) : 2687 - 2691
  • [3] Rh-Catalyzed Highly Enantioselective Hydrogenation of Functionalized Olefins with Chiral Ferrocenylphosphine-Spiro Phosphonamidite Ligands
    Chen, Yirui
    Yi, Xiao
    Cheng, Yuqi
    Huang, An
    Yang, Zehui
    Zhao, Xianghua
    Ling, Fei
    Zhong, Weihui
    JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (12): : 7864 - 7874
  • [4] Practical Rh(I)-catalyzed asymmetric hydrogenation of β-(acylamino)acrylates using a new unsymmetrical hybrid ferrocenylphosphine-phosphoramidite ligand:: Crucial influence of an N-H proton in the ligand
    Hu, XP
    Zhuo, Z
    ORGANIC LETTERS, 2005, 7 (03) : 419 - 422
  • [5] Unsymmetrical ferrocenylethylamine-derived monophosphoramidites:: Highly efficient chiral ligands for Rh-catalyzed enantioselective hydrogenation of enamides and α-dehydroamino acid derivatives
    Zeng, QH
    Hu, XP
    Duan, ZC
    Liang, XM
    Zheng, Z
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (01): : 393 - 396
  • [6] Readily available phosphine-phosphoramidite ligands for highly efficient Rh-catalyzed enantioselective hydrogenations
    Huang, Jia-Di
    Hu, Xiang-Ping
    Duan, Zheng-Chao
    Zeng, Qing-Hen
    Yu, Sai-Bo
    Deng, Jun
    Wang, Dao-Yong
    Zheng, Zhuo
    ORGANIC LETTERS, 2006, 8 (19) : 4367 - 4370
  • [7] Novel chiral phosphine-phosphoramidite ligands derived from 1-naphthylamine for highly efficient Rh-catalyzed asymmetric hydrogenation
    Yu, Sai-Bo
    Huang, Jia-Di
    Wang, Dao-Yong
    Hu, Xiang-Ping
    Deng, Jun
    Duan, Zheng-Chao
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2008, 19 (15) : 1862 - 1866
  • [8] Highly enantioselective rh-catalyzed hydrogenation based on phosphine-phosphite ligands derived from carbohydrates
    Pàmies, O
    Diéguez, M
    Net, G
    Ruiz, A
    Claver, C
    JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (25): : 8364 - 8369
  • [9] Highly enantioselective synthesis of α-hydroxy phosphonic acid derivatives by Rh-catalyzed asymmetric hydrogenation with phosphine-phosphoramidite ligands
    Wang, Dao-Yong
    Hu, Xiang-Ping
    Huang, Jia-Di
    Deng, Jun
    Yu, Sai-Bo
    Duan, Zheng-Chao
    Xu, Xue-Feng
    Zheng, Zhuo
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (41) : 7810 - 7813
  • [10] Me-AnilaPhos:: a new chiral phosphine-phosphoramidite ligand for a highly efficient Rh-catalyzed asymmetric olefin hydrogenation
    Vallianatou, Kalliopi A.
    Kostas, Ioannis D.
    Holz, Jens
    Boerner, Armin
    TETRAHEDRON LETTERS, 2006, 47 (45) : 7947 - 7950