Iridium-catalyzed enantioselective olefinic C(sp2)-H allylic alkylation

被引:15
|
作者
Sarkar, Rahul [1 ]
Mukherjee, Santanu [1 ]
机构
[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India
关键词
CYCLOADDITION;
D O I
10.1039/d0sc06208a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The first iridium-catalyzed enantioselective olefinic C(sp(2))-H allylic alkylation is developed in cooperation with Lewis base catalysis. This reaction, catalyzed by cinchonidine and an in situ generated cyclometalated Ir(i)/phosphoramidite complex, makes use of the latent enolate character of an alpha,beta-unsaturated carbonyl compound, namely coumalate ester, to introduce an allyl group at its alpha-position in a branched-selective manner in moderate to good yield with good to excellent enantioselectivities (up to 98 : 2 er).
引用
收藏
页码:3070 / 3075
页数:6
相关论文
共 50 条
  • [1] Hydroxy-directed iridium-catalyzed enantioselective formal β-C(sp2)-H allylic alkylation of α,β-unsaturated carbonyls
    Mitra, Sankash
    Sarkar, Rahul
    Chakrabarty, Aditya
    Mukherjee, Santanu
    CHEMICAL SCIENCE, 2022, 13 (42) : 12491 - 12497
  • [2] Iridium-Catalyzed Enantioselective Formal α-Allylic Alkylation of Acrylonitrile
    Roy, Pankaj
    Mukherjee, Santanu
    ORGANIC LETTERS, 2023, 25 (24) : 4520 - 4524
  • [3] Iridium-Catalyzed Enantioselective Allylic Alkylation with Functionalized Organozinc Bromides
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (26) : 7644 - 7647
  • [4] Iridium-catalyzed enantioselective direct vinylogous allylic alkylation of coumarins
    Sarkar, Rahul
    Mitra, Sankash
    Mukherjee, Santanu
    CHEMICAL SCIENCE, 2018, 9 (26) : 5767 - 5772
  • [5] Iridium-Catalyzed Enantioselective Allylic Substitution
    Takeuchi, Ryo
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2016, 74 (09) : 885 - 902
  • [6] Enantioselective Iridium-Catalyzed Allylic Cyclizations
    Schafroth, Michael A.
    Rummelt, Stephan M.
    Sarlah, David
    Carreira, Erick M.
    ORGANIC LETTERS, 2017, 19 (12) : 3235 - 3238
  • [7] Iridium-catalyzed enantioselective allylic vinylation
    Carreira, E.M. (carreira@org.chem.ethz.ch), 1600, American Chemical Society (135):
  • [8] Iridium-Catalyzed Enantioselective Allylic Alkynylation
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (29) : 7532 - 7535
  • [9] Enantioselective Iridium-Catalyzed Allylic Arylation
    Polet, Damien
    Rathgeb, Xavier
    Falciola, Caroline A.
    Langlois, Jean-Baptiste
    El Hajjaji, Samir
    Alexakis, Alexandre
    CHEMISTRY-A EUROPEAN JOURNAL, 2009, 15 (05) : 1205 - 1216
  • [10] Iridium-Catalyzed Enantioselective Allylic Vinylation
    Hamilton, James Y.
    Sarlah, David
    Carreira, Erick M.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (03) : 994 - 997