Rhodium-catalyzed enantioselective hydrogenation using chiral monophosphonite ligands

被引：137
|
作者：
Reetz, MT [1 ]
Sell, T [1 ]
机构：
[1] Max Planck Inst Kohlenforsch, D-45470 Mulheim, Germany
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 33期
关键词：
enantioselection; reduction; rhodium and compounds; phosphorus compounds; amino acids and derivatives;
D O I：
10.1016/S0040-4039(00)01099-6
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Surprisingly high enantioselectivities in the Rh-catalyzed hydrogenation of itaconic acid dimethyl eater and methyl-2-acetamido acrylate are observed upon using chiral monophosphonite ligands derived from binaphthol (ee up to 94%). Although appropriate chelating diphosphonites are more effective, the easy modular synthesis of the chiral monophosphonites may allow for the optimization of a given asymmetric hydrogenation reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：6333 / 6336
页数：4
相关论文
共 50 条
  • [1] NDIPhos as a platform for chiral supramolecular ligands in rhodium-catalyzed enantioselective hydrogenation
    Force, Guillaume
    Mayer, Robert J. J.
    Vayer, Marie
    Leboeuf, David
    CHEMICAL COMMUNICATIONS, 2023, 59 (41) : 6231 - 6234
  • [2] PhthalaPhos: Chiral Supramolecular Ligands for Enantioselective Rhodium-Catalyzed Hydrogenation Reactions
    Pignataro, Luca
    Carboni, Stefano
    Civera, Monica
    Colombo, Raffaele
    Piarulli, Umberto
    Gennari, Cesare
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (37) : 6633 - 6637
  • [3] 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
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (46) : 11539 - 11540
  • [4] 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
  • [5] Monodentate chiral spiro phosphoramidites: Efficient ligands for rhodium-catalyzed enantioselective hydrogenation of enamides
    Hu, AG
    Fu, Y
    Xie, JH
    Zhou, H
    Wang, LX
    Zhou, QL
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2002, 41 (13) : 2348 - 2350
  • [6] Chiral mixed phosphorus/sulfur ligands for rhodium-catalyzed enantioselective hydrogenation of didehydroaminoacids.
    Evans, DA
    Michael, FE
    Campos, KR
    Tedrow, JS
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U140 - U140
  • [7] Modular monodentate phosphoramidite ligands for rhodium-catalyzed enantioselective hydrogenation
    Liu, Yan
    Ding, Kuiling
    1600, American Chemical Society, Columbus, United States (127):
  • [8] Rhodium-Catalyzed Enantioselective Hydrogenation of Unsaturated Phosphonates by ClickFerrophos Ligands
    Konno, Takashi
    Shimizu, Kenta
    Ogata, Kenichi
    Fukuzawa, Shin-ichi
    JOURNAL OF ORGANIC CHEMISTRY, 2012, 77 (07): : 3318 - 3324
  • [9] Diphosphonites as highly efficient ligands for enantioselective rhodium-catalyzed hydrogenation
    Reetz, MT
    Gosberg, A
    Goddard, R
    Kyung, SH
    CHEMICAL COMMUNICATIONS, 1998, (19) : 2077 - 2078
  • [10] Modular monodentate phosphoramidite ligands for rhodium-catalyzed enantioselective hydrogenation
    Liu, Y
    Ding, KL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (30) : 10488 - 10489
12345