Enantioselective Rhodium-Catalyzed Coupling of Arylboronic Acids, 1,3-Enynes, and Imines by Alkenyl-to-Allyl 1,4-Rhodium(I) Migration

被引:43
|
作者
Callingham, Michael [1 ,2 ]
Partridge, Benjamin M. [1 ,3 ]
Lewis, William [1 ]
Lam, Hon Wai [1 ,2 ]
机构
[1] Univ Nottingham, Sch Chem, Univ Pk, Nottingham NG7 2RD, England
[2] Univ Nottingham, GSK Carbon Neutral Labs Sustainable Chem, Jubilee Campus,Triumph Rd, Nottingham NG7 2TU, England
[3] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England
基金
欧洲研究理事会; 英国工程与自然科学研究理事会;
关键词
allylation; asymmetric catalysis; imines; isomerization; rhodium; ALPHA; BETA-UNSATURATED DELTA-LACTONES; C-H FUNCTIONALIZATION; CHIRAL DIENE LIGANDS; CYCLIC IMINES; ASYMMETRIC CATALYSIS; CARBONYL-COMPOUNDS; NUCLEOPHILIC ALLYLATION; ALLENYL ALDEHYDES; PALLADIUM; KETIMINES;
D O I
10.1002/anie.201709334
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A chiral rhodium complex catalyzes the highly enantioselective coupling of arylboronic acids, 1,3-enynes, and imines to give homoallylic sulfamates. The key step is the generation of allylrhodium(I) species by alkenyl-to-allyl 1,4-rhodium(I) migration.
引用
收藏
页码:16352 / 16356
页数:5
相关论文
共 50 条
  • [1] Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration
    Partridge, Benjamin M.
    Callingham, Michael
    Lewis, William
    Lam, Hon Wai
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (25) : 7227 - 7232
  • [2] Rhodium(III)-Catalyzed [4+1] Oxidative Annulation of Amides with 1,3-enynes Through 1,4-Rhodium Migration
    Reddy, Chada Raji
    Subbarao, Muppidi
    Rathaur, Anjali
    Srinivasu, Ejjirotu
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (12) : 2036 - 2042
  • [3] Iridium-catalyzed 1,5-(aryl)aminomethylation of 1,3-enynes by alkenyl-to-allyl 1,4-iridium(i) migration
    Ruscoe, Rebecca E.
    Callingham, Michael
    Baker, Joshua A.
    Korkis, Stamatis E.
    Lam, Hon Wai
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (06) : 838 - 841
  • [4] Rhodium-catalyzed arylative cyclization of alkynyl malonates by 1,4-rhodium(i) migration
    O'Brien, Luke
    Karad, Somnath Narayan
    Lewis, William
    Lam, Hon Wai
    [J]. CHEMICAL COMMUNICATIONS, 2019, 55 (76) : 11366 - 11369
  • [5] Rhodium-catalyzed synthesis of 1-silabenzonorbornenes via 1,4-rhodium migration
    Shintani, Ryo
    Hama, Daichi
    Hamada, Naoya
    Miwa, Takuya
    [J]. TETRAHEDRON LETTERS, 2022, 104
  • [6] Rhodium-Catalyzed Dimerization of Arylacetylenes and Addition of Malonates to 1,3-Enynes
    Mochizuki, Katsufumi
    Sakai, Kazunori
    Kochi, Takuya
    Kakiuchi, Fumitoshi
    [J]. SYNTHESIS-STUTTGART, 2013, 45 (15): : 2088 - 2092
  • [7] Rhodium-catalyzed enantioselective 1,4-additions of arylboronic acids to substituted enones
    Urbaneja, LM
    Krause, N
    [J]. TETRAHEDRON-ASYMMETRY, 2006, 17 (04) : 494 - 496
  • [8] Rhodium-Catalyzed Polymerization of 3,3-Diarylcyclopropenes Involving a 1,4-Rhodium Migration
    Shintani, Ryo
    Iino, Ryo
    Nozaki, Kyoko
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (22) : 7849 - 7852
  • [9] Rhodium-catalyzed polymerization of 3,3-diarylcyclopropenes involving a 1,4-rhodium migration
    [J]. Shintani, R. (shintani@chembio.t.u-tokyo.ac.jp), 1600, American Chemical Society (136):
  • [10] Rhodium-catalyzed 1,4-hydroxyl migration of alkenyl alcohols
    Zhang, Xue
    Yan, Jiang-Min
    Zhang, Jia-Ning
    Xiong, Si-Qi
    Liang, Cheng
    Li, Qing-Hua
    Liu, Tang-Lin
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (19): : 5368 - 5373