Highly Enantioselective and Diastereoselective Synthesis of Chiral Amino Alcohols by Ruthenium-Catalyzed Asymmetric Hydrogenation of α-Amino Aliphatic Ketones

被引:69
|
作者
Xie, Jian-Hua
Liu, Sheng
Kong, Wei-Ling
Bai, Wen-Ju
Wang, Xiao-Chen
Wang, Li-Xin
Zhou, Qi-Lin [1 ]
机构
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
关键词
DYNAMIC KINETIC RESOLUTION; BETA-HYDROXY ESTERS; STEREOSELECTIVE HYDROGENATION; DERIVATIVES; RHODIUM; ROUTE;
D O I
10.1021/ja901058u
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A highly efficient asymmetric hydrogenation of racemic acyclic alpha-amino aliphatic ketones via dynamic kinetic resolution has been realized, providing chiral amino alcohols in excellent enantioselectivities and diastereoselectivities. A hydrogen-bonding transition state mode was proposed for explaining the high diastereoselectivity and enantioselectivity of the reaction.
引用
收藏
页码:4222 / +
页数:3
相关论文
共 50 条
  • [1] 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
  • [2] Ruthenium-Catalyzed Asymmetric Hydrogenation of β-Ketoenamines: An Efficient Approach to Chiral γ-Amino Alcohols
    Geng, Huiling
    Zhang, Xiaowei
    Chang, Mingxin
    Zhou, Le
    Wu, Wenjun
    Zhang, Xumu
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) : 3039 - 3043
  • [3] Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols
    Lu, Bin
    Wang, Qun
    Zhao, Mengmeng
    Xie, Xiaomin
    Zhang, Zhaoguo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9563 - 9569
  • [4] Highly Enantioselective Synthesis of Chiral Tetrahydroquinolines and Tetrahydroisoquinolines by Ruthenium-Catalyzed Asymmetric Hydrogenation in Ionic Liquid
    Ding, Zi-Yuan
    Wang, Tianli
    He, Yan-Mei
    Chen, Fei
    Zhou, Hai-Feng
    Fan, Qing-Hua
    Guo, Qingxiang
    Chan, Albert S. C.
    ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (18) : 3727 - 3735
  • [5] 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
  • [6] Asymmetric Ruthenium-Catalyzed Hydroalkylation of Racemic Allylic Alcohols for the Synthesis of Chiral Amino Acid Derivatives
    Zhang, Xiaohui
    Ma, Wei
    Zhang, Jinyu
    Tang, Weijun
    Xue, Dong
    Xiao, Jianliang
    Sun, Huaming
    Wang, Chao
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (26)
  • [7] Enantioselective Synthesis of Chiral 1,2-Amino Alcohols via Asymmetric Hydrogenation of α-Amino Ketones with Chiral Spiro Iridium Catalysts
    Yuan, Ming-Lei
    Xie, Jian-Hua
    Yang, Xiao-Hui
    Zhou, Qi-Lin
    SYNTHESIS-STUTTGART, 2014, 46 (21): : 2910 - 2916
  • [8] Synthesis of Chiral γ-Amino Alcohols via a RuPHOX-Ru Catalyzed Asymmetric Hydrogenation of β-Imide Ketones
    Wang, Yanzhao
    Wang, Jianxia
    Liu, Delong
    Zhang, Wanbin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (09) : 1766 - 1772
  • [9] Enantioselective addition of phenylacetylene to ketones catalyzed by chiral amino alcohols
    Ding Juan
    Shen Zong-Xuan
    Luo Xiao-Qing
    Chen Wei-Yi
    Zhang Ya-Wen
    CHINESE JOURNAL OF CHEMISTRY, 2006, 24 (10) : 1285 - 1289
  • [10] Highly efficient and enantioselective synthesis of β-heteroaryl amino alcohols via Ru-catalyzed asymmetric hydrogenation
    Wu, Chao
    Ma, Baode
    Chen, Gen-Qiang
    Zhang, Xumu
    CHEMICAL COMMUNICATIONS, 2022, 58 (91) : 12696 - 12699