Enantioselective copper(II)-catalyzed Henry reaction utilizing chiral aziridinyl alcohols

被引:10
|
作者
Wang, Xiaojuan [1 ]
Zhao, Wenxian [1 ,2 ]
Li, Gaowei [1 ]
Wang, Jin [2 ]
Liu, Guanjun [2 ]
Liu, Lantao [1 ]
Zhao, Ruijuan [2 ]
Wang, Mincan [2 ]
机构
[1] Shangqiu Normal Univ, Sch Chem & Chem Engn, Shangqiu 476000, Henan, Peoples R China
[2] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450052, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
aziridinyl alcohols; copper; asymmetric synthesis; Henry reaction; ASYMMETRIC NITROALDOL REACTION; AMINO-ALCOHOLS; LIGANDS; ALDEHYDES; DIETHYLZINC; CATALYST; COMPLEX; REDUCTION; DESIGN;
D O I
10.1002/aoc.3232
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
A family of enantiopure -aminoalcohols based on aziridine backbones were synthesized, and examined as chiral ligands for the copper(II)-catalyzed asymmetric Henry reaction of aromatic aldehydes with nitromethane, giving -nitroalcohols in excellent yields (up to 93%) and moderate to good enantioselectivities (up to 82%). Moreover, possible transition states of the reaction are proposed. Copyright (c) 2014 John Wiley & Sons, Ltd.
引用
收藏
页码:892 / 899
页数:8
相关论文
共 50 条
  • [21] Enantioselective nitroaldol (Henry) reaction catalyzed by chiral Schiff-base ligands
    Colak, Mehmet
    Demirel, Nadir
    TETRAHEDRON-ASYMMETRY, 2008, 19 (05) : 635 - 639
  • [22] Copper(II)-Catalyzed Hydrosilylation of Ketones Using Chiral Dipyridylphosphane Ligands: Highly Enantioselective Synthesis of Valuable Alcohols
    Yu, Feng
    Zhou, Ji-Ning
    Zhang, Xi-Chang
    Sui, Yao-Zong
    Wu, Fei-Fei
    Xie, Lin-Jie
    Chan, Albert S. C.
    Wu, Jing
    CHEMISTRY-A EUROPEAN JOURNAL, 2011, 17 (50) : 14234 - 14240
  • [23] The First Modular Route to Core-Chiral Bispidine Ligands and Their Application in Enantioselective Copper(II)-Catalyzed Henry Reactions
    Scharnagel, Dagmar
    Mueller, Andreas
    Prause, Felix
    Eck, Martin
    Goller, Jessica
    Milius, Wolfgang
    Breuning, Matthias
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (35) : 12488 - 12500
  • [24] Highly enantioselective nitroaldol reaction catalyzed by new chiral copper complexes
    Bandini, Marco
    Piccinelli, Fabio
    Tommasi, Simona
    Umani-Ronchi, Achille
    Ventrici, Caterina
    CHEMICAL COMMUNICATIONS, 2007, (06) : 616 - 618
  • [25] A new copper acetate-bis(oxazoline)-catalyzed, enantioselective Henry reaction
    Evans, DA
    Seidel, D
    Rueping, M
    Lam, HW
    Shaw, JT
    Downey, CW
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (42) : 12692 - 12693
  • [26] Copper-Catalyzed Enantioselective Henry Reaction of β,γ-Unsaturated α-Ketoesters with Nitromethane in Water
    Li, Yanan
    Huang, Yekai
    Gui, Yang
    Sun, Jianan
    Li, Jindong
    Zha, Zhenggen
    Wang, Zhiyong
    ORGANIC LETTERS, 2017, 19 (23) : 6416 - 6419
  • [27] Enantioselective nitroaldol (Henry) reaction using copper(II) complexes of (-)-sparteine
    Maheswaran, H.
    Prasanth, K. Leon
    Krishna, G. Gopi
    Ravikumar, K.
    Sridhar, B.
    Kantam, M. Lakshmi
    CHEMICAL COMMUNICATIONS, 2006, (39) : 4066 - 4068
  • [28] Henry Reaction Revisited. Crucial Role of Water in an Asymmetric Henry Reaction Catalyzed by Chiral NNO-Type Copper(II) Complexes
    Larionov, Vladimir A.
    Yashkina, Lidiya V.
    Medvedev, Michael G.
    Smol'yakov, Alexander F.
    Peregudov, Alexander S.
    Pavlov, Alexander A.
    Eremin, Dmitry B.
    Savel'yeva, Tat'yana F.
    Maleev, Victor I.
    Belokon, Yuri N.
    INORGANIC CHEMISTRY, 2019, 58 (16) : 11051 - 11065
  • [29] Novel bifunctional chiral thiourea catalyzed highly enantioselective aza-Henry reaction
    Wang, Chungui
    Zhou, Zhenghong
    Tang, Chuchi
    ORGANIC LETTERS, 2008, 10 (09) : 1707 - 1710
  • [30] Highly Enantioselective Aza-Henry Reaction of Ketoimines Catalyzed by Chiral N,N′-Dioxide-Copper(I) Complexes
    Tan, Cheng
    Liu, Xiaohua
    Wang, Liwei
    Wang, Jun
    Feng, Xiaoming
    ORGANIC LETTERS, 2008, 10 (22) : 5305 - 5308