Nickel-Catalyzed Enantioselective α-Allylation of Cyclic Ketones with Allylic Alcohols

被引:1
|
作者
Jiang, Neng-Quan [1 ,2 ]
Li, Ming-Ming [1 ,2 ]
Xiao, Li-Jun [1 ,2 ]
Zhou, Qi-Lin [1 ,2 ]
机构
[1] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, State Key Lab, Tianjin 300071, Peoples R China
[2] Nankai Univ, Coll Chem, Frontiers Sci Ctr New Organ Matter, Inst Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
Allylic alcohol; Ketone; Allylic alkylation; Enantioselectivity; Nickel catalysis; ASYMMETRIC ALKYLATION; QUATERNARY; SUBSTITUTION; KETOESTERS; LIGANDS; ETHERS;
D O I
10.1002/adsc.202400538
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Transition-metal-catalyzed asymmetric alpha-allylation of ketones is a particularly useful tool for constructing stereocenters via C-C bond formation. However, this type of reaction often necessitated the use of activated ketones or pre-prepared enol intermediates as substrates. In this study, we developed a nickel-catalyzed alpha-allylation of unactivated cycloketones with allylic alcohols to synthesize chiral cycloketones with an alpha-quaternary carbon center. The reaction affords the products with 42-97% yields, 72-86% ee, and no additive is needed, and the only by-product is water. image
引用
收藏
页码:3829 / 3832
页数:4
相关论文
共 50 条
  • [31] NICKEL-CATALYZED ASYMMETRIC ALKYLATION OF SOME CHIRAL AND ACHIRAL ALLYLIC ALCOHOLS
    CONSIGLIO, G
    MORANDINI, F
    PICCOLO, O
    HELVETICA CHIMICA ACTA, 1980, 63 (04) : 987 - 989
  • [32] Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes
    Yi-Xuan Cao
    Matthew D. Wodrich
    Nicolai Cramer
    Nature Communications, 14
  • [33] Nickel-Catalyzed Alkylation or Reduction of Allylic Alcohols with Alkyl Grignard Reagents
    Yang, Bo
    Wang, Zhong-Xia
    JOURNAL OF ORGANIC CHEMISTRY, 2020, 85 (07): : 4772 - 4784
  • [34] Nickel-catalyzed direct stereoselective α-allylation of ketones with non-conjugated dienes
    Cao, Yi-Xuan
    Wodrich, Matthew D.
    Cramer, Nicolai
    NATURE COMMUNICATIONS, 2023, 14 (01)
  • [35] Nickel-Catalyzed Redox-Economical Coupling of Alcohols and Alkynes to Form Allylic Alcohols
    Nakai, Kenichiro
    Yoshida, Yuji
    Kurahashi, Takuya
    Matsubara, Seijiro
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) : 7797 - 7800
  • [36] Enantioselective nickel-catalyzed electrochemical reductive conjugate alkenylation of α,β-unsaturated ketones
    Somprasong, Siriphong
    Wan, Bin
    Harutyunyan, Syuzanna R.
    CHEMICAL SCIENCE, 2025, 16 (02) : 802 - 808
  • [37] Nickel-Catalyzed Enantioselective Reductive Amination of Ketones with Both Arylamines and Benzhydrazide
    Yang, Peng
    Lim, Li Hui
    Chuanprasit, Pratanphorn
    Hirao, Hajime
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (39) : 12083 - 12087
  • [38] Nickel-catalyzed cross-electrophile coupling of aryl chlorides with allylic alcohols
    Yu, Hang
    Wang, Zhong-Xia
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (44) : 9723 - 9731
  • [39] Neutral nickel-catalyzed dehydrosulfonylation of unactivated allylic alcohols under mild conditions
    Yang, Yahui
    Zhu, Haibo
    Gong, Bozhen
    Yang, Hong
    Fan, Qiangwen
    Le, Zhang-Gao
    Xie, Zongbo
    CHEMICAL COMMUNICATIONS, 2024, 60 (18) : 2516 - 2519
  • [40] A substrate-dependent mechanism for nickel-catalyzed N-allylation with allylic alcohols: nucleophilic attack vs. reductive elimination
    Yao, Ruiming
    Jing, Yaru
    Liu, Jiahao
    Liu, Yan
    Wang, Tiejun
    Ke, Zhuofeng
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (11) : 2721 - 2727