Copper-Catalyzed Regio- and Enantioselective Synthesis of Chiral Enol Acetates and β-Substituted Aldehydes

被引：34
|
作者：
Fananas-Mastral, Martin [1 ]
Feringa, Ben L. [1 ]
机构：
[1] Univ Groningen, Stratingh Inst Chem, NL-9747 AG Groningen, Netherlands
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2010年 / 132卷 / 38期
关键词：
ASYMMETRIC CONJUGATE ADDITION; LIGANDS; KETONES;
D O I：
10.1021/ja105585y
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The in situ transformation of alpha,beta-unsaturated aldehydes into alpha-chloroallylic acetates and subsequent copper-catalyzed regio- and enantioselective (up to 94% ee) allylic alkylation with Grignard reagents provides chiral enol acetates and chiral beta-substituted aldehydes in a one-pot protocol.
引用
收藏
页码：13152 / 13153
页数：2
相关论文
共 50 条
  • [1] Copper-Catalyzed Regio- and Enantioselective Hydroboration of Difluoroalkyl-Substituted Internal Alkenes
    Zhao, Tao-Qian
    Xu, Hui
    Tian, Yu-Chen
    Tang, Xiaodong
    Dang, Yanfeng
    Ge, Shaozhong
    Ma, Jun-An
    Zhang, Fa-Guang
    ADVANCED SCIENCE, 2023, 10 (35)
  • [2] Highly Regio- and Enantioselective Copper-Catalyzed Hydroboration of Styrenes
    Noh, Dongwan
    Chea, Heesung
    Ju, Junghwan
    Yun, Jaesook
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) : 6062 - 6064
  • [3] Copper-Catalyzed Regio- and Enantioselective Hydroamination of Alkenes with Hydroxylamines
    Hesp, Kevin D.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (08) : 2034 - 2036
  • [4] Photoinduced Copper-Catalyzed Regio- and Enantioselective Alkynylation of Epoxides
    Li, Jianye
    Li, Sijia
    Cui, Guo-Hao
    Yuan, Kaiyao
    Wang, Chenwei
    Yang, Chen
    Zhang, Guozhu
    Guo, Rui
    ACS CATALYSIS, 2024, 14 (10): : 7553 - 7561
  • [5] Copper-Catalyzed Regio- and Enantioselective Protoboration of Allenyl Sulfones to Access Chiral Allylic Sulfones
    Sun, Peidong
    Kong, Xiaomei
    Huang, Jingwen
    Ma, Xuedi
    Xu, Tongyu
    Zeng, Fanlong
    JOURNAL OF ORGANIC CHEMISTRY, 2025, 90 (08): : 3022 - 3033
  • [6] Copper-Catalyzed Regio- and Enantioselective Aminoboration of Unactivated Terminal Alkenes
    Kato, Kodai
    Hirano, Koji
    Miura, Masahiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2018, 24 (22) : 5775 - 5778
  • [7] Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination
    Ichikawa, Saki
    Dai, Xi-Jie
    Buchwald, Stephen L.
    ORGANIC LETTERS, 2019, 21 (11) : 4370 - 4373
  • [8] Copper-catalyzed regio- and enantioselective aminoboration of alkylidenecyclopropanes: the synthesis of cyclopropane-containing β-aminoalkylboranes
    Jiang, Han-Chun
    Tang, Xiang-Ying
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2016, 52 (30) : 5273 - 5276
  • [9] Copper-catalyzed regio- and enantioselective formal conjugate addition of Grignard reagents to a,b-unsaturated aldehydes
    Mastral, Martin Fananas
    Feringa, Ben L.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [10] Copper-catalyzed intermolecular Regio- and Enantioselective Hydrosilylation of Alkenes with Prochiral Silanes
    Zhu, Xiao-Yan
    Gao, Wenyu
    Xu, Jian-Lin
    Wang, Zi-Lu
    Zhao, Jin-Bo
    Xu, Yun-He
    NATURE COMMUNICATIONS, 2025, 16 (01)
12345