Highly Chemo-, Regio-, and Enantioselective Rhodium-Catalyzed Cross-Cyclotrimerization of Two Different Alkynes with Alkenes

被引:39
|
作者
Hara, Jun [1 ]
Ishida, Mana [1 ]
Kobayashi, Masayuki [1 ]
Noguchi, Keiichi [2 ]
Tanaka, Ken [1 ,3 ]
机构
[1] Tokyo Univ Agr & Technol, Dept Appl Chem, Grad Sch Engn, Koganei, Tokyo 1848588, Japan
[2] Tokyo Univ Agr & Technol, Instrumentat Anal Ctr, Koganei, Tokyo 1848588, Japan
[3] Japan Sci & Technol Agcy JST, ACT C, Kawaguchi, Saitama 3320012, Japan
基金
日本科学技术振兴机构;
关键词
alkenes; alkynes; asymmetric catalysis; cyclotrimerization; multicomponent reactions; rhodium; REGIOSELECTIVE INTERMOLECULAR CYCLOTRIMERIZATION; 3 UNSYMMETRICAL ALKYNES; BORON TEMPORARY TETHER; LIQUID ENOL ETHERS; 2+2+2 CYCLOADDITION; ETHYL CYCLOPROPYLIDENEACETATE; TERMINAL ALKYNES; NICKEL; COMPLEXES; PYRIDINES;
D O I
10.1002/anie.201310336
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
It has been established that a cationic rhodium(I)/(R)-tol-binap complex catalyzes the cross-cyclotrimerization of silylacetylenes, di-tert-butyl acetylenedicarboxylates, and acrylamides with excellent chemo-, regio-, and enantioselectivities. Unsymmetrical alkynoates can also be employed in place of di-tert-butyl acetylenedicarboxylate for this process, but with reduced chemoselectivity.
引用
收藏
页码:2956 / 2959
页数:4
相关论文
共 50 条
  • [41] Rhodium-catalyzed regio- and stereoselective 1-seleno-2-thiolation of 1-alkynes
    Arisawa, M
    Kozuki, Y
    Yamaguchi, M
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (23): : 8964 - 8967
  • [42] Highly Regio-, Diastereo-, and Enantioselective Rhodium-Catalyzed Intramolecular Cyclopropanation of (Z)-1,3-Dienyl Aryldiazoacetates
    Marichev, Kostiantyn O.
    Ramey, Justin T.
    Arman, Hadi
    Doyle, Michael P.
    ORGANIC LETTERS, 2017, 19 (06) : 1306 - 1309
  • [43] Highly Enantioselective Rhodium-Catalyzed Cross-Addition of Silylacetylenes to Cyclohexadienone-Tethered Internal Alkynes
    Duan, Chang-Lin
    Tan, Yun-Xuan
    Zhang, Jun-Li
    Yang, Shiping
    Dong, Han-Qing
    Tian, Ping
    Lin, Guo-Qiang
    ORGANIC LETTERS, 2019, 21 (06) : 1690 - 1693
  • [44] Rhodium-Catalyzed Highly Enantioselective Hydroboration of Acyclic Tetrasubstituted Alkenes Directed by an Amide
    Lu, Hou-Xiang
    Wang, Cheng
    Gao, Tao-Tao
    Lin, En-Ze
    Lu, Shou-Lin
    Hong, Xin
    Li, Bi-Jie
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (23) : 16194 - 16202
  • [45] Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes
    Institut für Organische Chemie, Albert-Ludwigs-Universität Freiburg, Albertstrasse 21, Freiburg im Breisgau
    79104, Germany
    Angew. Chem. Int. Ed., 24 (7149-7153):
  • [46] Regio- and Enantioselective Synthesis of N-Substituted Pyrazoles by Rhodium-Catalyzed Asymmetric Addition to Allenes
    Haydl, Alexander M.
    Xu, Kun
    Breit, Bernhard
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (24) : 7149 - 7153
  • [47] Chiral Selenide-Catalyzed, Highly Regio- and Enantioselective Intermolecular Thioarylation of Alkenes with Phenols
    Zhang, Yuanyuan
    Liang, Yaoyu
    Zhao, Xiaodan
    ACS CATALYSIS, 2021, 11 (06) : 3755 - 3761
  • [48] Development of chemo-, regio-, and enantioselective [2+2+2] cycloadditions catalyzed by cationic Rhodium(I)/BINAP-type bisphosphine complexes
    Tanaka, Ken
    Nishida, Goushi
    Suda, Takeshi
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2007, 65 (09) : 862 - 873
  • [49] Cobalt-catalyzed highly regio- and stereoselective intermolecular reductive coupling of alkynes with conjugated alkenes
    Wang, CC
    Lin, PS
    Cheng, CH
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (33) : 9696 - 9697
  • [50] Rhodium-catalyzed regio-, diastereo-, and enantioselective intermolecular [4+2] carbocyclization of 4-alkynals with electron-deficient alkenes
    Tanaka, Ken
    Hagiwara, Yuji
    Hirano, Masao
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (16) : 3582 - 3595