Synthesis of new functionalized chiral ionic liquid and its organocatalytic asymmetric epoxidation in water

被引：20
|
作者：
Li, Jian [2 ]
Hu, Feng [2 ]
Xie, Xiao-Ke [2 ]
Liu, Feiyan [1 ]
Huang, Zhi-Zhen [2 ]
机构：
[1] Zhejiang Univ, Coll Life Sci, Hangzhou 310058, Zhejiang, Peoples R China
[2] Nanjing Univ, Sch Chem & Chem Engn, Nanjing 210093, Peoples R China
来源：
CATALYSIS COMMUNICATIONS | 2009年 / 11卷 / 04期
基金：
中国国家自然科学基金;
关键词：
Functionalized chiral ionic liquid; Organocatalyst; Epoxidation; Water; Recycle; Green asymmetric synthesis; SULFUR YLIDES; CARBONYL-COMPOUNDS; SULFONIUM YLIDES; CATALYTIC CYCLE; ALDEHYDES; EPOXIDES; MECHANISM; SULFIDES; AZIRIDINATION; GENERATION;
D O I：
10.1016/j.catcom.2009.10.014
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
A new sulfur-functionalized chiral ionic liquid has been developed for the epoxidation reaction of aromatic aldehydes with benzyl bromide in water, furnishing desired trans-epoxides with excellent diastereoselectivity and enantioselectivity up to 72% ee. The organocatalyst could be easily reused for five times without remarkable decrease in yields and enantioselectivities. (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码：276 / 279
页数：4
相关论文
共 50 条
  • [31] Epoxidation of styrene and its derivatives catalyzed by a multi-component ionic liquid functionalized with manganese porphyrin
    Mang Hongjiao
    Liu Ye
    Cai Yueqin
    Wu Haihong
    Liu Xiuli
    CHINESE JOURNAL OF CATALYSIS, 2008, 29 (02) : 127 - 133
  • [32] Asymmetric Synthesis of Axially Chiral Arylpyrazole via an Organocatalytic Arylation Reaction
    Gao, Xi
    Li, Chengwen
    Chen, Li
    Li, Xin
    ORGANIC LETTERS, 2023, 25 (42) : 7628 - 7632
  • [33] Immobilization of Chiral Quininium Salt in Ionic Liquid for Enantioselective Epoxidation of Chalcones
    Pal, Ravindra R.
    Dere, Ravindra T.
    Patil, Prashant S.
    SubbaReddy, Basi V.
    Salunkhe, Manikrao M.
    LETTERS IN ORGANIC CHEMISTRY, 2009, 6 (04) : 332 - 334
  • [34] Organocatalytic asymmetric synthesis of chiral fluorinated quaternary carbon containing β-ketoesters
    Li, Hao
    Zhang, Shilei
    Yu, Chenguang
    Song, Xixi
    Wang, Wei
    CHEMICAL COMMUNICATIONS, 2009, (16) : 2136 - 2138
  • [35] Asymmetric Synthesis of Chiral Oxazolines by Organocatalytic Cyclization of α-Aryl Isocyanoesters with Aldehydes
    Xue, Meng-Xia
    Guo, Chang
    Gong, Liu-Zhu
    SYNLETT, 2009, (13) : 2191 - 2197
  • [36] Organocatalytic Asymmetric syn-Selective Direct Aldol Reaction in Ionic Liquid
    Yong, Fui-Fong
    Poh, Chai-Yun
    Chua, Guan-Leong
    Teo, Yong-Chua
    CHEMISTRY LETTERS, 2010, 39 (05) : 490 - 492
  • [37] Functionalized chiral ionic liquid catalyzed enantioselective desymmetrizations of prochiral ketones via asymmetric Michael addition reaction
    Luo, Sanzhong
    Zhang, Long
    Mi, Xueling
    Qiao, Yupu
    Cheng, Jin-Pei
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9350 - 9352
  • [38] Combinatorial synthesis of functionalized chiral and doubly chiral ionic liquids and their applications as asymmetric covalent/non-covalent bifunctional organocatalysts
    Zhang, Long
    Luo, Sanzhong
    Mi, Xueling
    Liu, Song
    Qiao, Yupu
    Xu, Hui
    Cheng, Jin-Pei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2008, 6 (03) : 567 - 576
  • [39] Asymmetric SN1 α-Alkylation of Cyclic Ketones Catalyzed by Functionalized Chiral Ionic Liquid (FCIL) Organocatalysts
    Zhang, Long
    Cui, Lingyun
    Li, Xin
    Li, Jiuyuan
    Luo, Sanzhong
    Cheng, Jin-Pei
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (07) : 2045 - 2049
  • [40] Chiral vanadium phosphonates: Synthesis, characterization, and applications to heterogeneous asymmetric epoxidation
    Macor, Joseph A.
    Girolami, Gregory S.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 246
12345