Highly chemo- and enantioselective arylative cyclization of alkyne-tethered electron-deficient olefins catalyzed by rhodium complexes with chiral dienes

被引:120
|
作者
Shintani, R [1 ]
Tsurusaki, A [1 ]
Okamoto, K [1 ]
Hayashi, T [1 ]
机构
[1] Kyoto Univ, Grad Sch Sci, Dept Chem, Sakyo Ku, Kyoto 6068502, Japan
关键词
asymmetric catalysis; chemoselectivity; cyclization; diene ligands; rhodium;
D O I
10.1002/anie.200500843
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Chemical Equation Presented) A rhodium catalyst promotes the arylative cyclization of alkyne-tethered electron-deficient olefins in the presence of aryl boronic acids. High chemoselectivity was attained uniquely by the use of diene ligands, and high enantioselectivity was successfully realized by employing a C2-symmetric chiral bicyclo[2.2.2]octadiene ligand (see scheme). © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:3909 / 3912
页数:4
相关论文
共 13 条
  • [1] Rhodium-Catalyzed Highly Regio- and Enantioselective Reductive Cyclization of Alkyne-Tethered Cyclohexadienones
    Gollapelli, Krishna Kumar
    Donikela, Sangeetha
    Manjula, Nemali
    Chegondi, Rambabu
    ACS CATALYSIS, 2018, 8 (02): : 1440 - 1447
  • [2] Cationic Pd(II)-Catalyzed Highly Enantioselective Arylative Cyclization of Alkyne-Tethered Enals or Enones Initiated by Carbopalladation of Alkynes with Arylboronic Acids
    Shen, Kun
    Han, Xiuling
    Lu, Xiyan
    ORGANIC LETTERS, 2012, 14 (07) : 1756 - 1759
  • [3] Highly enantioselective Diels-Alder reactions of Danishefsky type dienes with electron-deficient alkenes catalyzed by Yb(III)-BINAMIDE complexes
    Sudo, Yukinori
    Shirasaki, Daisuke
    Harada, Shinji
    Nishida, Atsushi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (38) : 12588 - +
  • [5] Highly enantioselective hydroformylation of olefins catalyzed by Rhodium(I) complexes of new chiral phosphine-phosphite ligands
    Nozaki, K
    Sakai, N
    Nanno, T
    Higashijima, T
    Mano, S
    Horiuchi, T
    Takaya, H
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (19) : 4413 - 4423
  • [6] Rhodium(I)/Chiral Diene Complexes Catalyzed Asymmetric Desymmetrization of Alkynyl-Tethered 2,5-Cyclohexadienones Through an Arylative Cyclization Cascade
    Cheng, Yu-Yi
    Kuo, Ting-Shen
    Wu, Ping-Yu
    Hsieh, Jen-Chieh
    Wu, Hsyueh-Liang
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (07): : 4861 - 4876
  • [7] tert-Butanesulfinylphosphines: Simple Chiral Ligands in Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to Electron-Deficient Olefins
    Lang, Feng
    Li, Dong
    Chen, Junmin
    Chen, Jun
    Li, Liangchun
    Cun, Linfeng
    Zhu, Jin
    Deng, Jingen
    Liao, Jian
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (05) : 843 - 846
  • [8] Highly Stereoselective Conjugate Addition and -Alkynylation Reaction with Electron-Deficient Alkynes Catalyzed by Chiral Scandium(III) Complexes
    Wang, Zhen
    Zhang, Zuliang
    Yao, Qian
    Liu, Xiaohua
    Cai, Yunfei
    Lin, Lili
    Feng, Xiaoming
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (26) : 8591 - 8596
  • [9] Highly enantioselective Diels-Alder reaction of Danishefsky-type diene and electron-deficient olefins catalyzed by an Yb(III)/chiral bis-urea complex
    Harada, Shinji
    Toudou, Nozomi
    Hiraoka, Shiharu
    Nishida, Atsushi
    TETRAHEDRON LETTERS, 2009, 50 (40) : 5652 - 5655
  • [10] Enantioselective Conjugate Addition of Aryl Halides and Triflates to Electron-Deficient Olefins via Nickel- and Rhodium-Catalyzed Sequential Relay Reactions
    Fan, Chenrui
    Wu, Qixu
    Zhu, Chengfeng
    Wu, Xiang
    Li, Yougui
    Luo, Yunfei
    He, Jian-Bo
    ORGANIC LETTERS, 2019, 21 (22) : 8888 - 8892