Cobalt-Catalyzed Asymmetric 1,6-Addition of (Triisopropylsilyl)-acetylene to α,β,γ,δ-Unsaturated Carbonyl Compounds

被引:86
|
作者
Sawano, Takahiro [1 ]
Ashouri, Akram [1 ]
Nishimura, Takahiro [1 ]
Hayashi, Tamio [2 ]
机构
[1] Kyoto Univ, Dept Chem, Grad Sch Sci, Kyoto 6068502, Japan
[2] ASTAR, Inst Mat Res & Engn, Singapore 117602, Singapore
关键词
ENANTIOSELECTIVE 1,6-CONJUGATE ADDITION; SELECTIVE LINEAR CODIMERIZATION; CONJUGATE ADDITION; TERMINAL ALKYNES; GRIGNARD-REAGENTS; ALPHA; BETA-UNSATURATED THIOAMIDES; ENONES; SILYLACETYLENES; ACETYLENES; COMPLEXES;
D O I
10.1021/ja309756k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Asymmetric addition of (triisopropylsilyl)-acetylene to alpha,beta,gamma,delta-unsaturated carbonyl compounds took place in the presence of a cobalt/Duphos catalyst to give the 1,6-addition products in high yields with high regio- and enantioselectivity.
引用
收藏
页码:18936 / 18939
页数:4
相关论文
共 50 条
  • [31] Asymmetric conjugate 1,6-addition of organocuprates to N-dienoyl oxazolidinones
    Sansinenea, Estibaliz
    Martinez, Edith Fabiola
    Vaca, Jessica
    Gonzalez-Alvarez, Carmen M.
    Ortiz, Aurelio
    TETRAHEDRON, 2024, 166
  • [32] Copper-Catalyzed Asymmetric 1,6-Addition of Borylalkene-Derived Nucleophiles to para-Quinone Methides
    Meng, Deyuan
    He, Jing
    Yoon, Woojin
    Yun, Hoseop
    Han, Jung Tae
    Yun, Jaesook
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (23) : 4135 - 4140
  • [33] Rhodium-Catalyzed Enantioselective 1,6-Addition of Arylboronic Acids to Enynamides: Asymmetric Synthesis of Axially Chiral Allenylsilanes
    Nishimura, Takahiro
    Makino, Hiroki
    Nagaosa, Makoto
    Hayashi, Tamio
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (37) : 12865 - 12867
  • [34] Enantioselective Cobalt-Catalyzed Intermolecular Hydroacylation of 1,6-Enynes
    Whyte, Andrew
    Bajohr, Jonathan
    Torelli, Alexa
    Lautens, Mark
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (38) : 16409 - 16413
  • [35] Cobalt-Catalyzed Cyclization/Hydroboration of 1,6-Diynes with Pinacolborane
    Huang, Qiang
    Hu, Meng-Yang
    Zhu, Shou-Fei
    ORGANIC LETTERS, 2019, 21 (19) : 7883 - 7887
  • [36] Cobalt-catalyzed cascade hydroalkenylation of 1,6-enynes with chalcones
    Pan, Chunxiang
    Wang, Gaowei
    Zhao, Hengyuan
    Ni, Jianxiao
    Fan, Ruifeng
    Zhou, Yongyun
    Zhu, Yuanbin
    Wu, Shiyuan
    Fan, Baomin
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (06) : 1616 - 1620
  • [37] Low-Temperature Rh-Catalyzed Asymmetric 1,4-Addition of Arylboronic Acids to α,β-Unsaturated Carbonyl Compounds
    Korenaga, Toshinobu
    Ko, Aram
    Shimada, Kazuaki
    JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (19): : 9975 - 9980
  • [38] Asymmetric addition of P-H compounds to unsaturated carbonyl derivatives
    Rapi, Zsolt
    Orban, Istvan
    ARKIVOC, 2022,
  • [39] Nickel-Catalyzed Regiodivergent Asymmetric Cycloadditions of ?,?-Unsaturated Carbonyl Compounds
    Cao, Shi
    Ye, Ziqi
    Chen, Yuehua
    Lin, Yu-Mei
    Fang, Jiahua
    Wang, Yuejiao
    Yang, Boxuan
    Gong, Lei
    CCS CHEMISTRY, 2022, 4 (09): : 3122 - 3133
  • [40] Rhodium-catalyzed asymmetric hydrogenation of exocyclic α,β-unsaturated carbonyl compounds
    Yang, Jiaxin
    Li, Xiuxiu
    You, Cai
    Li, Shuailong
    Guan, Yu-Qing
    Lv, Hui
    Zhang, Xumu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (05) : 856 - 859