Asymmetric hydrogenolysis of racemic 3-substitued-3-hydroxy-isoindolin-1-ones employing SPINOL-derived chiral phosphoric acid

被引:12
|
作者
Zhang, Yiliang [1 ,2 ]
He, Li [1 ,2 ]
Shi, Lei [1 ,2 ]
机构
[1] Harbin Inst Technol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China
[2] Harbin Inst Technol, Sch Chem & Chem Engn, MIIT Key Lab Crit Mat Technol New Energy Convers, Harbin 150001, Heilongjiang, Peoples R China
关键词
Asymmetric catalysis; Chiral phosphoric acid; Hydrogenolysis; Hantzsch ester; IONIC HYDROGENATION; BENZYLIC ALCOHOLS; TERTIARY ALCOHOLS; SYNTHETIC METHODS; FORMIC-ACID; ISOINDOLINONES; EFFICIENT; FLUORIDE; TRIETHYLSILANE; PHSCF2SIME3;
D O I
10.1016/j.tetlet.2018.03.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The asymmetric hydrogenolysis of racemic 3-substitued-3-hydroxyisoindolin-1-ones has been developed employing SPINOL-derived phosphoric acid and a high steric demand Hantzsch ester as the hydrogen source. The corresponding products are obtained in good yields and up to 93% enantioselectivities. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1592 / 1595
页数:4
相关论文
共 32 条
  • [1] Chiral phosphoric acid catalyzed asymmetric hydrogenolysis of racemic 3-aryl-3-hydroxyisoindolin-1-ones
    Zhou, Jian-Qing
    Sheng, Wei-Jian
    Jia, Jian-Hong
    Ye, Qing
    Gao, Jian-Rong
    Jia, Yi-Xia
    TETRAHEDRON LETTERS, 2013, 54 (24) : 3082 - 3084
  • [2] Asymmetric hydrogenolysis of racemic tertiary alcohols, 3-substituted 3-hydroxyisoindolin-1-ones
    Chen, Mu-Wang
    Chen, Qing-An
    Duan, Ying
    Ye, Zhi-Shi
    Zhou, Yong-Gui
    CHEMICAL COMMUNICATIONS, 2012, 48 (11) : 1698 - 1700
  • [3] Development of Immobilized SPINOL-Derived Chiral Phosphoric Acids for Catalytic Continuous Flow Processes. Use in the Catalytic Desymmetrization of 3,3-Disubstituted Oxetanes
    Lai, Junshan
    Fianchini, Mauro
    Pericas, Miquel A.
    ACS CATALYSIS, 2020, 10 (24): : 14971 - 14983
  • [4] Chiral Phosphoric Acid Catalyzed Asymmetric Friedel-Crafts Alkylation of Indole with 3-Hydroxyisoindolin-1-one: Enantioselective Synthesis of 3-Indolyl-Substituted Isoindolin-1-ones
    Yu, Xiaolei
    Lu, Aidang
    Wang, Youming
    Wu, Guiping
    Song, Haibin
    Zhou, Zhenghong
    Tang, Chuchi
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (05) : 892 - 897
  • [5] Chiral Phosphoric Acid Catalyzed Asymmetric Mannich Reaction of 2-Aryl-3H-indol-3-ones with α-H Diazoacetates
    Lin, Cheng
    He, Jia-Hao
    Rao, Ming-Liang
    Yang, Gui-Ping
    Li, Wen-Jie
    Zhou, Meng
    Zhao, Chong
    Fu, Xiao-Zhong
    He, Bin
    Zhao, Yong-Long
    ORGANIC LETTERS, 2025,
  • [6] The asymmetric synthesis of CF3- or -CF2-substituted tetrahydroquinolines by employing a chiral phosphoric acid as catalyst
    Lin, Jin-Hong
    Zong, Guoqiang
    Du, Ruo-Bing
    Xiao, Ji-Chang
    Liu, Shubin
    CHEMICAL COMMUNICATIONS, 2012, 48 (62) : 7738 - 7740
  • [7] Chiral phosphoric acid-catalysed Friedel-Crafts alkylation reaction of indoles with racemic spiro indolin-3-ones
    Yin, Qin
    You, Shu-Li
    CHEMICAL SCIENCE, 2011, 2 (07) : 1344 - 1348
  • [8] Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)-butanoic acid derived from threonine
    Gallagher, John F.
    Brady, Fiona
    Murphy, Carol
    Acta Crystallographica, Section C: Crystal Structure Communications, 2000, 56 (03) : 365 - 368
  • [9] Intermolecular interactions in the chiral and racemic forms of 3-hydroxy-2-(1-oxoisoindolin-2-yl)butanoic acid derived from threonine
    Gallagher, JF
    Brady, F
    Murphy, C
    ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2000, 56 : 365 - 368
  • [10] Asymmetric [3+3] cycloaddition of cinnamaldehyde-derived N-aryl nitrones with 2-indolemethanols enabled by chiral phosphoric acid
    Zou, Ning
    Wu, Yu-Zheng
    Shang, Zi-Wei
    Cao, Yu-Wei
    Liao, Li-Min
    Wei, Cui
    Mo, Dong-Liang
    Zhou, Wen-Jun
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (46) : 9047 - 9052