An enantioselective synthesis of 3-aryl-4-phosphonobutyric acid esters via Cu-catalyzed asymmetric conjugate reduction

被引：8
|
作者：
Guo, Wei-Lei [1 ,2 ]
Hou, Chuan-Jin [1 ]
Duan, Zheng-Chao [2 ]
Hu, Xiang-Ping [2 ]
机构：
[1] Dalian Polytech Univ, Sch Light Ind & Chem Engn, Dalian 116034, Peoples R China
[2] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China
来源：
TETRAHEDRON-ASYMMETRY | 2011年 / 22卷 / 24期
关键词：
DYNAMIC KINETIC-RESOLUTION; BOPHOZ-TYPE LIGAND; ALPHA; BETA-UNSATURATED ESTERS; DIASTEREOSELECTIVE SYNTHESIS; HYDROGENATION; PHOSPHONATES; DERIVATIVES; INHIBITORS; HYDROXYPHOSPHONATES; HYDROSILYLATIONS;
D O I：
10.1016/j.tetasy.2011.12.009
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
The asymmetric conjugate reduction of 3-aryl-4-phosphonobutenoates has been demonstrated which provides an enantioselective synthesis of optically active 3-aryl-4-phosphonobutyric acid esters. A wide range of 3-aryl-4-phosphonobutenoate derivates are reduced with high enantioselectivities (up to 94% ee) using an (S)-Segphos/Cu(OAc)(2)center dot H2O catalyst system (1 or 5 mol %) in the presence of PMHS and t-BuOH. The reduction is influenced by the steric and electronic effects of the substrates. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2161 / 2164
页数：4
相关论文
共 50 条
  • [1] Cu(II)-Catalyzed Enantioselective Conjugate Reduction for the Synthesis of N-Aryl β-Amino Acid Esters
    Sui Yaozong
    Fang Qiang
    Li Min
    Hu Yihu
    Xia Hongfeng
    Li Shijun
    Wu Jing
    CHINESE JOURNAL OF CHEMISTRY, 2012, 30 (11) : 2611 - 2614
  • [2] Enantioselective synthesis of β-aryl-γ-amino acid derivatives via Cu-catalyzed asymmetric 1,4-reductions of γ-phthalimido-substituted α,β-unsaturated carboxylic acid esters
    Deng, Jun
    Hu, Xiang-Ping
    Huang, Jia-Di
    Yu, Sai-Bo
    Wang, Dao-Yong
    Duan, Zheng-Chao
    Zheng, Zhuo
    JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (15): : 6022 - 6024
  • [3] Diastereo- and Enantioselective Synthesis of α,γ-Diaminobutyric Acid Derivatives via Cu-Catalyzed Asymmetric Michael Reaction
    Li, Qing
    Ding, Chang-Hua
    Hou, Xue-Long
    Dai, Li-Xin
    ORGANIC LETTERS, 2010, 12 (05) : 1080 - 1083
  • [4] Catalytic Asymmetric Synthesis of Sulfinamides via Cu-Catalyzed Asymmetric Addition of Aryl Boroxines to Sulfinylamines
    Shi, Yixiang
    Yuan, Yin
    Li, Jianhui
    Yang, Junfeng
    Zhang, Junliang
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (26) : 17580 - 17586
  • [5] Chiral ferrocenyl phosphine-phosphoramidite ligands for Cu-catalyzed asymmetric conjugate reduction of α,β-unsaturated esters
    Hou, Chuan-Jin
    Guo, Wei-Lei
    Hu, Xiang-Ping
    Deng, Jun
    Zheng, Zhuo
    TETRAHEDRON-ASYMMETRY, 2011, 22 (02) : 195 - 199
  • [6] Enantioselective Synthesis of (R)-Tolterodine via CuH-Catalyzed Asymmetric Conjugate Reduction
    Yoo, Kihyun
    Kim, Hyohyun
    Yun, Jaesook
    JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (11): : 4232 - 4235
  • [7] Enantioselective Synthesis of Boryl Tetrahydroquinolines via Cu-Catalyzed Hydroboration
    Kong, Duanyang
    Han, Suna
    Zi, Guofu
    Hou, Guohua
    Zhang, Jiaxin
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (04): : 1924 - 1932
  • [8] Cu-catalyzed enantioselective conjugate addition of alkylzincs to cyclic nitroalkenes:: Catalytic asymmetric synthesis of cyclic α-substituted ketones
    Luchaco-Cullis, CA
    Hoveyda, AH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (28) : 8192 - 8193
  • [9] Cu-Catalyzed Enantioselective Hydrogermylation: Asymmetric Synthesis of Unnatural β-Germyl α-Amino Acids
    Lin, Weidong
    You, Lijun
    Yuan, Wei
    He, Chuan
    ACS CATALYSIS, 2022, 12 (23) : 14592 - 14600
  • [10] Cu-Catalyzed Asymmetric Hydroboration of Naphthylallylic Compounds for Enantioselective Synthesis of Chiral Boronates
    Han, Suna
    Shen, Xin
    Kong, Duanyang
    Zi, Guofu
    Hou, Guohua
    Zhang, Jiaxin
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (07): : 4318 - 4329
12345