Rhodium(I)-Catalyzed [2+2+1] cycloadditions of 1,3-dienes, alkenes, and CO

被引：50
|
作者：
Wender, PA [1 ]
Croatt, MP [1 ]
Deschamps, NM [1 ]
机构：
[1] Stanford Univ, Dept Chem, Stanford, CA 94305 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 19期
关键词：
D O I：
10.1021/ja0489487
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Initial examples of a Rh(I)-catalyzed [2+2+1] reaction of diene-enes and CO are described. This method allows for the facile, efficient, and diastereoselective construction of a variety of alkenyl cyclopentanones in good to excellent yields. Control studies show that the diene moiety is required for this process as bis-enes do not give the [2+2+1] products under the same conditions. Copyright © 2003 American Chemical Society.
引用
收藏
页码：5948 / 5949
页数：2
相关论文
共 50 条
  • [41] Regiodivergent Copper Catalyzed Borocyanation of 1,3-Dienes
    Jia, Tao
    He, Qiong
    Ruscoe, Rebecca E.
    Pulis, Alexander P.
    Procter, David J.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (35) : 11305 - 11309
  • [42] Organoselenium-Catalyzed Regioselective C-H Pyridination of 1,3-Dienes and Alkenes
    Liao, Lihao
    Guo, Ruizhi
    Zhao, Xiaodan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (12) : 3201 - 3205
  • [43] Mechanistic study on the regioselectivity of Co-catalyzed hydroacylation of 1,3-dienes
    Yuan-Ye Jiang
    Hai-Zhu Yu
    Jing Shi
    ChineseChemicalLetters, 2015, 26 (01) : 58 - 62
  • [44] Rhodium-catalyzed regio- and stereoselective codimerization of alkenes and electron-deficient internal alkynes leading to 1,3-dienes
    Shibata, Yu
    Hirano, Masao
    Tanaka, Ken
    ORGANIC LETTERS, 2008, 10 (13) : 2829 - 2831
  • [45] Mechanistic study on the regioselectivity of Co-catalyzed hydroacylation of 1,3-dienes
    Jiang, Yuan-Ye
    Yu, Hai-Zhu
    Shi, Jing
    CHINESE CHEMICAL LETTERS, 2015, 26 (01) : 58 - 62
  • [46] ASYMMETRIC DOUBLE HYDROBORATION OF 1,3-DIENES CATALYZED BY CHIRAL PHOSPHINE-RHODIUM COMPLEXES
    MATSUMOTO, Y
    HAYASHI, T
    TETRAHEDRON LETTERS, 1991, 32 (28) : 3387 - 3390
  • [47] Rh(i)-Catalyzed enantioselective and scalable [4+2] cycloaddition of 1,3-dienes with dialkyl acetylenedicarboxylates
    Bao, Robert Li-Yuan
    Yin, Junjie
    Shi, Lei
    Zheng, Limin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (15) : 2956 - 2961
  • [48] Intermolecular Hydroamination of 1,3-Dienes Catalyzed by Bis(phosphine)carbodicarbene-Rhodium Complexes
    Goldfogel, Matthew J.
    Roberts, Courtney C.
    Meek, Simon J.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (17) : 6227 - 6230
  • [49] Pd-Catalyzed Regioselective Cyclopropanation of 2-Substituted 1,3-Dienes
    Kastrati, Agonist
    Jaquier, Vincent
    Garbo, Michele
    Besnard, Ceïline
    Mazet, Cleïment
    ACS ORGANIC & INORGANIC AU, 2023, 3 (05): : 291 - 298
  • [50] CYCLIC CO-OLIGOMERIZATION OF 2-VINYLFURAN WITH 1,3-DIENES, CATALYZED BY NICKEL-COMPLEXES
    TOLSTIKOV, GA
    DZHEMILEV, UM
    GUBAIDULLIN, LY
    ZHURNAL ORGANICHESKOI KHIMII, 1976, 12 (08): : 1645 - 1650
12345