Highly enantioselective hydrogenation of α-dehydroamino acids by rhodium complex with H8-MonoPhos

被引:64
作者
Zeng, Q
Liu, H
Cui, X
Mi, AQ
Jiang, YZ [1 ]
Li, XS
Choi, MCK
Chan, ASC
机构
[1] Chinese Acad Sci, Chengdu Inst Organ Chem, Union Lab Asymmetr Synth, Chengdu 610041, Peoples R China
[2] Hong Kong Polytech Univ, Open Lab Chirotechnol, Hong Kong, Hong Kong, Peoples R China
[3] Hong Kong Polytech Univ, Dept Appl Biol & Chem Technol, Hong Kong, Hong Kong, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/S0957-4166(02)00096-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
H-8-MonoPhos, a new stable and easily prepared monodentate phosphoramidite ligand, has been synthesized from H-8-BINOL. The ligand showed extremely highly enantioselectivity of higher than 99.9% e.e. in the asymmetric Rh-catalyzed hydrogenation of alpha-dehydroamino acids. Our study further supports the new concept that there is no gap in efficiency and enantioselectivity between monodentate and chelating ligands for asymmetric catalysis. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:115 / 117
页数:3
相关论文
共 14 条
  • [1] Novel asymmetric alkylation of aromatic aldehydes with triethylaluminum catalyzed by titanium (1,1'-bi-2-naphthol) and titanium (5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol) complexes
    Chan, ASC
    Zhang, FY
    Yip, CW
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (17) : 4080 - 4081
  • [2] Claver C, 2000, CHEM COMMUN, P961
  • [3] Reduction of 1,1′-binaphthyls to octahydro-1,1′-binaphthyl derivatives with Raney Ni-Al alloy in aqueous solution
    Guo, H
    Ding, KL
    [J]. TETRAHEDRON LETTERS, 2000, 41 (51) : 10061 - 10064
  • [4] Rhodium-catalyzed enantioselective hydrogenation using chiral monophosphonite ligands
    Reetz, MT
    Sell, T
    [J]. TETRAHEDRON LETTERS, 2000, 41 (33) : 6333 - 6336
  • [5] Reetz MT, 2000, ANGEW CHEM INT EDIT, V39, P3889, DOI 10.1002/1521-3773(20001103)39:21<3889::AID-ANIE3889>3.0.CO
  • [6] 2-T
  • [7] Highly efficient enantioselective synthesis of optically active carboxylic acids by Ru(OCOCH3)(2)[(S)-H-8-BINAP]
    Uemura, T
    Zhang, XY
    Matsumura, K
    Sayo, N
    Kumobayashi, H
    Ohta, T
    Nozaki, K
    Takaya, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (16) : 5510 - 5516
  • [8] Highly enantioselective rhodium-catalyzed hydrogenation with monodentate ligands
    van den Berg, M
    Minnaard, AJ
    Schudde, EP
    van Esch, J
    de Vries, AHM
    de Vries, JG
    Feringa, BL
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11539 - 11540
  • [9] Highly efficient enantioselective synthesis of optically active dihydropyrones by chiral titanium(iv) (5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol) complexes
    Wang, B
    Feng, XM
    Cui, X
    Liu, H
    Jiang, YZ
    [J]. CHEMICAL COMMUNICATIONS, 2000, (17) : 1605 - 1606
  • [10] Zhang FY, 1997, TETRAHEDRON-ASYMMETR, V8, P585, DOI 10.1016/S0957-4166(97)00024-4