Copper-Catalyzed Enantioselective Henry Reaction of β,γ-Unsaturated α-Ketoesters with Nitromethane in Water

被引：29
|
作者：
Li, Yanan
Huang, Yekai
Gui, Yang
Sun, Jianan
Li, Jindong
Zha, Zhenggen
Wang, Zhiyong [1 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, CAS Key Lab Soft Matter Chem, Hefei 230026, Anhui, Peoples R China
来源：
ORGANIC LETTERS | 2017年 / 19卷 / 23期
关键词：
ASYMMETRIC NITROALDOL REACTIONS; DIELS-ALDER REACTION; CARBON-CARBON BOND; ORGANIC-REACTIONS; AQUEOUS-MEDIA; STEREOSELECTIVE CONSTRUCTION; SELECTIVE SYNTHESIS; EFFICIENT SYNTHESIS; DANISHEFSKYS DIENE; HYDROXY ESTERS;
D O I：
10.1021/acs.orglett.7b03299
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly enantioselective Henry reaction of beta,gamma-unsaturated alpha-ketoesters with nitromethane in water by virtue of chiral copper complexes has been developed. A series of unsaturated beta-nitro-alpha-hydroxy esters bearing tetrasubstituted carbon stereocenters were obtained exclusively with high yields and excellent enantioselectivities. This method could avoid tedious anaerobic anhydrous manipulation and reduce the environmental pollution caused by organic solvents.
引用
收藏
页码：6416 / 6419
页数：4
相关论文
共 50 条
  • [1] Enantioselective Copper-Catalyzed Conjugate Addition of Trimethylaluminium to β,γ-Unsaturated α-Ketoesters
    Gremaud, Ludovic
    Alexakis, Alexandre
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (03) : 794 - 797
  • [2] Copper-Catalyzed Enantioselective Hetero-Diels-Alder Reaction of Danishefsky's Diene with β,γ-Unsaturated α-Ketoesters
    Hu, Yanbin
    Xu, Kun
    Zhang, Sheng
    Guo, Fengfeng
    Zha, Zhenggen
    Wang, Zhiyong
    ORGANIC LETTERS, 2014, 16 (13) : 3564 - 3567
  • [3] Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters
    Deng, Qing-Hai
    Wadepohl, Hubert
    Gade, Lutz H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) : 10769 - 10772
  • [4] Copper-Catalyzed Chemoselective and Enantioselective Friedel Crafts 1,2-Addition of Pyrrole with β,γ-Unsaturated α-Ketoesters
    Sun, Jianan
    Hu, Yanbin
    Li, Yanan
    Zhang, Sheng
    Zha, Zhenggen
    Wang, Zhiyong
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (10): : 5102 - 5110
  • [5] Stereoselective Copper-Catalyzed Direct Aldol Reaction of β, γ-Unsaturated α-Ketoesters with Coumaran-3-Ones
    Li, Kuiliang
    Sun, Xiang
    Li, Linge
    Zha, Zhenggen
    Zhang, Feng-Lian
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (02) : 581 - 584
  • [6] Copper-Catalyzed Sonogashira Reaction in Water
    Liu, Yujia
    Blanchard, Vincent
    Danoun, Gregory
    Zhang, Zhaoyang
    Tlili, Anis
    Zhang, Wenlong
    Monnier, Florian
    Van der Lee, Arie
    Mao, Jincheng
    Taillefer, Marc
    CHEMISTRYSELECT, 2017, 2 (35): : 11599 - 11602
  • [7] Highly enantioselective henry (nitroaldol) reaction of aldehydes and α-ketoesters catalyzed by N,N′-Dioxide-Copper(I) complexes
    Qin, Bo
    Xiao, Xiao
    Liu, Xiaohua
    Huang, Jinglun
    Wen, Yuehong
    Feng, Xiaoming
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (24): : 9323 - 9328
  • [8] Synthesis of novel chiral bisoxazoline ligands with a norbornadiene backbone: use in the copper-catalyzed enantioselective Henry reaction
    Delikus, Rabia
    Cakir, Emine
    Demirel, Nadir
    Balci, Metin
    Karatas, Betul
    TURKISH JOURNAL OF CHEMISTRY, 2016, 40 (02) : 248 - 261
  • [9] Enantioselective Copper(I/II)-Catalyzed Conjugate Addition of Nitro Esters to β,γ-Unsaturated α-Ketoesters
    Zhang, Sheng
    Xu, Kun
    Guo, Fengfeng
    Hu, Yanbin
    Zha, Zhenggen
    Wang, Zhiyong
    CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (04) : 979 - 982
  • [10] Copper-Catalyzed Enantioselective Henry Reaction of Enals and Subsequent Iodocyclization: Stereoselective Construction of Chiral Azatricyclic Frameworks
    Zhou, Yirong
    Zhu, Yuequan
    Yan, Shaobai
    Gong, Yuefa
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (39) : 10265 - 10269
12345