Copper-catalyzed enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins

被引：18
|
作者：
Li, Jindong [1 ,2 ,3 ]
Li, Yanan [1 ,2 ,3 ]
Sun, Jianan [1 ,2 ,3 ]
Gui, Yang [1 ,2 ,3 ]
Huang, Yekai [1 ,2 ,3 ]
Zha, Zhenggen [1 ,2 ,3 ]
Wang, Zhiyong [1 ,2 ,3 ]
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
[2] Univ Sci & Technol China, Ctr Excellence Mol Synth, Chinese Acad Sci, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Hefei 230026, Anhui, Peoples R China
[3] Univ Sci & Technol China, Sch Chem & Mat Sci, Hefei 230026, Anhui, Peoples R China
来源：
CHEMICAL COMMUNICATIONS | 2019年 / 55卷 / 44期
关键词：
BETA; GAMMA-UNSATURATED ALPHA-KETOESTERS; LEWIS-BASE ACTIVATION; DIELS-ALDER REACTION; AQUEOUS-MEDIA; REACTION; 40YEARS; ACID CATALYSTS; HENRY REACTION; WATER; ALDEHYDES; LIGANDS;
D O I：
10.1039/c9cc02159k
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A highly enantioselective Mukaiyama aldol reaction of silyl enol ethers with isatins was developed. A series of chiral 3-substituted 3-hydroxy-2-oxindoles could be obtained exclusively with high yields (up to 95%) and excellent enantioselectivities (up to 99%). In particular, water was essential to improve the diastereoselectivity.
引用
收藏
页码：6309 / 6312
页数：4
相关论文
共 50 条
  • [1] Copper-Catalyzed Enantioselective Mukaiyama Aldol Reaction of Silyl Enol Ethers with Isatin-Derived Oxindolyl β,γ-Unsaturated α-Keto Esters
    Lu, Wenjing
    Li, Jindong
    Lu, Yangmian
    Zha, Zhenggen
    Wang, Zhiyong
    [J]. CHEMISTRYSELECT, 2021, 6 (03): : 410 - 414
  • [2] Enantioselective copper-catalyzed cyclopropanation of silyl enol ethers
    Ebinger, A
    Heinz, T
    Umbricht, G
    Pfaltz, A
    [J]. TETRAHEDRON, 1998, 54 (35) : 10469 - 10480
  • [3] N-Triflylthiophosphoramide Catalyzed Enantioselective Mukaiyama Aldol Reaction of Aldehydes with Silyl Enol Ethers of Ketones
    Cheon, Cheol Hong
    Yamamoto, Hisashi
    [J]. ORGANIC LETTERS, 2010, 12 (11) : 2476 - 2479
  • [4] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE CATALYSIS OF THE MUKAIYAMA ALDOL REACTION - ENE MECHANISM IN TITANIUM-CATALYZED ALDOL REACTIONS OF SILYL ENOL ETHERS
    MIKAMI, K
    MATSUKAWA, S
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (15) : 7039 - 7040
  • [5] Enantioselective O-nitroso aldol reaction of silyl enol ethers
    Kawasaki, Masanori
    Li, Pingfan
    Yamamoto, Hisashi
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (20) : 3795 - 3797
  • [6] Acetaldehyde Silyl Enol Ethers in Enantioselective Mukaiyama Aldol Reactions: Enzyme-Like Organocatalysis in Action
    Dell'Amico, Luca
    Zanardi, Franca
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (11) : 3264 - 3266
  • [7] A Cu-BOX catalysed enantioselective Mukaiyama-aldol reaction with difluorinated silyl enol ethers and acylpyridine N-oxides
    Sanz-Marco, Amparo
    Esperilla, Daniel
    Montesinos-Magraner, Marc
    Vila, Carlos
    Carmen Munoz, M.
    Pedro, Jose R.
    Blay, Gonzalo
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2023, 21 (02) : 345 - 350
  • [8] Highly stereoselective construction of adjacent tetrasubstituted carbon stereogenic centres via an organocatalytic Mukaiyama-aldol reaction of monofluorinated silyl enol ethers to isatins
    Liu, Yun-Lin
    Liao, Fu-Min
    Niu, Yan-Fei
    Zhao, Xiao-Li
    Zhou, Jian
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (07): : 742 - 747
  • [9] An efficient catalyst-free Mukaiyama-aldol reaction of fluorinated enol silyl ethers with tryptanthrin
    Liao, Fu-Min
    Liu, Yun-Lin
    Yu, Jin-Sheng
    Zhou, Feng
    Zhou, Jian
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (33) : 8906 - 8911
  • [10] Copper-Catalyzed Fluoroolefination of Silyl Enol Ethers and Ketones toward the Synthesis of β-Fluoroenones
    Li, Yanlin
    Liu, Jing
    Zhao, Shuang
    Du, Xuzhao
    Guo, Minjie
    Zhao, Wentao
    Tang, Xiangyang
    Wang, Guangwei
    [J]. ORGANIC LETTERS, 2018, 20 (04) : 917 - 920
12345