Enantioselective Synthesis of Chiral β-Aryloxy Alcohols by Ruthenium-Catalyzed Ketone Hydrogenation via Dynamic Kinetic Resolution (DKR)

被引：33
|
作者：
Bai, Wen-Ju
Xie, Jian-Hua
Li, Ya-Li
Liu, Sheng
Zhou, Qi-Lin [1 ]
机构：
[1] Nankai Univ, State Key Lab, Tianjin 300071, Peoples R China
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 01期
基金：
中国国家自然科学基金;
关键词：
beta-aryloxy alcohols; asymmetric hydrogenation; dynamic kinetic resolution; ketones; ruthenium; EFFICIENT ASYMMETRIC HYDROGENATION; METAL-COMPLEXES; HYDROXY AMINES; DERIVATIVES;
D O I：
10.1002/adsc.200900675
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly efficient enantioselective synthesis of chiral beta-aryloxy alcohols by the {RuCl2[(S)-SDP][(R,R)-DPEN]} [(S-a,R,R)-1a; SDP=7,7'-bis-(diarylphosphino)-1,1'-spirobiindane; DPEN=trans-1,2-diphenylethylenediamine] complex-catalyzed asymmetric hydrogenation of racemic alpha-aryloxydialkyl ketones via dynamic kinetic resolution (DKR) has been developed. Enantioselectivities of up to 99% ee with good to high cis/anti-selectivities (up to > 99:1) were achieved.
引用
收藏
页码：81 / 84
页数：4
相关论文
共 50 条
  • [1] Enantioselective Synthesis of Chiral β-Aryloxy Alcohols by Asymmetric Hydrogenation of α-Aryloxy Aldehydes via Dynamic Kinetic Resolution
    Zhou, Zhang-Tao
    Xie, Jian-Hua
    Zhou, Qi-Lin
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (03) : 363 - 366
  • [2] Synthetic applications of the ruthenium-catalyzed hydrogenation via dynamic kinetic resolution
    Ratovelomanana-Vidal, V
    Genêt, JP
    [J]. CANADIAN JOURNAL OF CHEMISTRY, 2000, 78 (06) : 846 - 851
  • [3] General synthesis of chiral β-hydroxy sulfones via enantioselective ruthenium-catalyzed hydrogenation
    Bertus, P
    Phansavath, P
    Ratovelomanana-Vidal, V
    Genêt, JP
    Touati, AR
    Homri, T
    Ben Hassine, B
    [J]. TETRAHEDRON LETTERS, 1999, 40 (16) : 3175 - 3178
  • [4] 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
    [J]. ORGANIC LETTERS, 2009, 11 (21) : 4994 - 4997
  • [5] 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
    [J]. ORGANIC LETTERS, 2020, 22 (11) : 4322 - 4326
  • [6] Dynamic kinetic resolution allows a highly enantioselective synthesis of cis-α-aminocycloalkanols by ruthenium-catalyzed asymmetric hydrogenation
    Liu, Sheng
    Xie, Jian-Hua
    Wang, Li-Xin
    Zhou, Qi-Lin
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (39) : 7506 - 7508
  • [7] Ruthenium-Catalyzed Enantioselective Hydrogenation of Ferrocenyl Ketones: A Synthetic Method for Chiral Ferrocenyl Alcohols
    Lu, Bin
    Wang, Qun
    Zhao, Mengmeng
    Xie, Xiaomin
    Zhang, Zhaoguo
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19): : 9563 - 9569
  • [8] Highly Enantioselective and Diastereoselective Synthesis of Chiral Amino Alcohols by Ruthenium-Catalyzed Asymmetric Hydrogenation of α-Amino Aliphatic Ketones
    Xie, Jian-Hua
    Liu, Sheng
    Kong, Wei-Ling
    Bai, Wen-Ju
    Wang, Xiao-Chen
    Wang, Li-Xin
    Zhou, Qi-Lin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (12) : 4222 - +
  • [9] Efficient ruthenium-catalyzed racemization of secondary alcohols: application to dynamic kinetic resolution
    Dijksman, A
    Elzinga, JM
    Li, YX
    Arends, IWCE
    Sheldon, RA
    [J]. TETRAHEDRON-ASYMMETRY, 2002, 13 (08) : 879 - 884
  • [10] Enantioselective and Diastereoselective Construction of Chiral Amino Alcohols by Iridium-f-Amphox-Catalyzed Asymmetric Hydrogenation via Dynamic Kinetic Resolution
    Wu, Weilong
    You, Cai
    Yin, Congcong
    Liu, Yuanhua
    Dong, Xiu-Qin
    Zhang, Xumu
    [J]. ORGANIC LETTERS, 2017, 19 (10) : 2548 - 2551
12345