Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of Allylic Alcohols by an Enantioselective Isomerization/Transfer Hydrogenation Mechanism

被引:56
|
作者
Wu, Ruoqiu [1 ]
Beauchamps, Marie G. [1 ]
Laquidara, Joseph M. [1 ]
Sowa, John R., Jr. [1 ]
机构
[1] Seton Hall Univ, Dept Chem & Biochem, S Orange, NJ 07079 USA
关键词
allylic alcohols; asymmetric catalysis; asymmetric transfer hydrogenation; isomerization; phosphine ligands; REDOX ISOMERIZATION; EFFICIENT; KETONES; REDUCTION; COMPLEXES; SCOPE; LIGANDS;
D O I
10.1002/anie.201107910
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Reducing hazards: A asymmetric transfer hydrogen reaction was developed to reduce prochiral allylic alcohols in high yield and excellent enantioselectivity (see example). Mechanistic studies indicate a novel enantioselective isomerization/transfer hydrogenation mechanism. This new reaction is much safer than high-pressure hydrogenation using H 2 gas. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2106 / 2110
页数:5
相关论文
共 50 条
  • [21] Chiral β-Amino Alcohols as Ligands for the Ruthenium-Catalyzed Asymmetric Transfer Hydrogenation of N-Phosphinyl Ketimines
    Pablo, Oscar
    Guijarro, David
    Yus, Miguel
    APPLIED SCIENCES-BASEL, 2012, 2 (01): : 1 - 12
  • [22] Highly Enantioselective Synthesis of Chiral Cyclic Amino Alcohols and Conhydrine by Ruthenium-Catalyzed Asymmetric Hydrogenation
    Liu, Sheng
    Xie, Jian-Hua
    Li, Wei
    Kong, Wei-Ling
    Wang, Li-Xin
    Zhou, Qi-Lin
    ORGANIC LETTERS, 2009, 11 (21) : 4994 - 4997
  • [23] Ruthenium catalyzed asymmetric transfer hydrogenation of β-ketoesters
    Everaere, K
    Carpentier, JF
    Mortreux, A
    Bulliard, M
    TETRAHEDRON-ASYMMETRY, 1998, 9 (17) : 2971 - 2974
  • [24] Ruthenium-Catalyzed Highly Enantioselective Synthesis of cis-3-Quinuclidinols via DKR Asymmetric Transfer Hydrogenation
    Luo, Zhonghua
    Wang, Zhongqing
    Sun, Guodong
    Jian, Weilin
    Jiang, Fengkai
    Luan, Baolei
    Li, Ridong
    Zhang, Lei
    ORGANIC LETTERS, 2020, 22 (11) : 4322 - 4326
  • [25] Mechanism studies of Ru-catalysed asymmetric transfer hydrogenation of allylic alcohols
    Wu, Ruoqiu
    Beauchamps, Marie G.
    Laquidara, Joseph M.
    Sowa, John R.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 244
  • [26] 2-azanorbornyl alcohols: Very efficient ligands for ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones
    Alonso, DA
    Nordin, SJM
    Roth, P
    Tarnai, T
    Andersson, PG
    Thommen, M
    Pittelkow, U
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 3116 - 3122
  • [27] Ruthenium-Catalyzed Enantioselective Hydrogenation of Phenanthridine Derivatives
    Yang, Zhusheng
    Chen, Fei
    Zhang, Shuxin
    He, Yanmei
    Yang, Nianfa
    Fan, Qing-Hua
    ORGANIC LETTERS, 2017, 19 (06) : 1458 - 1461
  • [28] Ruthenium-catalyzed enantioselective hydrogenation of quinoxalinones and quinazolinones
    Li, Chenghao
    Zhang, Shuxin
    Li, Shan
    Feng, Yu
    Fan, Qing-Hua
    Organic Chemistry Frontiers, 2022, 9 (02) : 400 - 406
  • [29] Ruthenium-catalyzed enantioselective hydrogenation of quinoxalinones and quinazolinones
    Li, Chenghao
    Zhang, Shuxin
    Li, Shan
    Feng, Yu
    Fan, Qing-Hua
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (02): : 400 - 406
  • [30] RUTHENIUM-CATALYZED ISOMERIZATION OF ALLYLIC ALCOHOLS TO SATURATED KETONES
    BACKVALL, JE
    ANDREASSON, U
    TETRAHEDRON LETTERS, 1993, 34 (34) : 5459 - 5462