Efficient synthesis of chiral benzofuryl β-amino alcohols via a catalytic asymmetric Henry reaction

被引:18
|
作者
Chen, Wei [1 ]
Zhou, Zhao-Hui [1 ]
Chen, Hong-Bin [1 ]
机构
[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Peoples R China
关键词
BLOCKING-AGENT; BUFURALOL-HCL; COMPLEX; PROPAFENONE; ALDEHYDES; (S)-BUFURALOL; PROPRANOLOL; RESISTANCE; ANALOGS;
D O I
10.1039/c6ob02569b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral beta-amino alcohol ligands were found effective for the copper(II)-catalyzed asymmetric Henry reaction of benzofuran-2-carbaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl beta-nitro alcohols with satisfactory enantioselectivities (up to 98% ee). Using this catalytic protocol, bioactive (S)-benzofuryl beta-amino alcohols could be conveniently prepared in short steps.
引用
收藏
页码:1530 / 1536
页数:7
相关论文
共 50 条
  • [41] An oxazaborolidine-based catalytic method for the asymmetric synthesis of chiral allylic alcohols
    Yildiz, Tulay
    TETRAHEDRON-ASYMMETRY, 2015, 26 (8-9) : 497 - 504
  • [42] Efficient Synthesis of β-Hydroxy-α-Amino Acid Derivatives via Direct Catalytic Asymmetric Aldol Reaction of α-Isothiocyanato Imide with Aldehydes
    Chen, Xiaohong
    Zhu, Yin
    Qiao, Zhen
    Xie, Mingsheng
    Lin, Lili
    Liu, Xiaohua
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (33) : 10124 - 10129
  • [43] The synthesis of chiral β-aryl-α,β-unsaturated amino alcohols via a Pd-catalyzed asymmetric allylic amination
    Quan, Mao
    Butt, Nicholas
    Shen, Jiefeng
    Shen, Kaiji
    Liu, Delong
    Zhang, Wanbin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (42) : 7412 - 7419
  • [44] Synthesis of Chiral Secondary β-amino Alcohols and their Application in the Asymmetric Reduction of Prochiral Ketones
    Ran, De-Qiang
    Shen, Tian-Hua
    Zhou, Xiao-Cong
    Ma, Chun-An
    Song, Qing-Bao
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2013, 35 (01): : 125 - 129
  • [45] Synthesis and characterization of chiral recyclable dimeric copper(II)-salen complexes and their catalytic application in asymmetric nitroaldol (Henry) reaction
    Das, Anjan
    Kureshy, Rukhsana I.
    Subramanian, P. S.
    Khan, Noor-ul H.
    Abdi, Sayed H. R.
    Bajaj, Hari C.
    CATALYSIS SCIENCE & TECHNOLOGY, 2014, 4 (02) : 411 - 418
  • [46] 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
  • [47] Asymmetric synthesis of fluoroalkyl amino compounds via chiral sulfoxides
    Bravo, P
    Bruché, L
    Crucianelli, M
    Viani, M
    Zanda, M
    ASYMMETRIC FLUOROORGANIC CHEMISTRY: SYNTHESIS, APPLICATIONS, AND FUTURE DIRECTIONS, 2000, 746 : 98 - 116
  • [48] Asymmetric synthesis of fluoroalkyl amino compounds via chiral sulfoxides
    Bravo, Pierfrancesco
    Bruche, Luca
    Crucianelli, Marcello
    Viani, Fiorenza
    Zanda, Matteo
    ACS Symposium Series, 746 : 98 - 116
  • [49] Simple and efficient synthesis of chiral amino alcohols with an amino acid-based skeleton
    Paulina Juszczyk
    Regina Kasprzykowska
    Aleksandra S. Kołodziejczyk
    Letters in Peptide Science, 2003, 10 (2): : 79 - 82
  • [50] 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