Regio- and enantioselective ring-opening reaction of vinylcyclopropanes with indoles under cooperative catalysis

被引:22
|
作者
Wan, Xiao [1 ]
Sun, Meng [1 ]
Wang, Jing-Yi [1 ]
Yu, Lei [1 ]
Wu, Qiong [2 ]
Zhang, Yu-Chen [1 ]
Shi, Feng [1 ]
机构
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Peoples R China
[2] Xuzhou Univ Technol, Sch Mat & Chem Engn, Xuzhou 221018, Jiangsu, Peoples R China
基金
中国国家自然科学基金;
关键词
ASYMMETRIC ALLYLIC ALKYLATION; FORMAL 3+2 CYCLOADDITION; VINYL CYCLOPROPANES; TRANSITION-METAL; IN-SITU; CONSTRUCTION; BOND; CYCLOPENTANES; CYCLIZATION; EXPANSION;
D O I
10.1039/d0qo00699h
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title reaction has been established under the cooperative bimetallic catalysis of iridium and copper catalysts, which afforded indole C3-allylation products with branched selectivity in moderate yields (up to 78%) and good enantioselectivities (up to 97 : 3 er). This reaction not only represents the first catalytic asymmetric ring-opening reaction of vinylcyclopropanes with C3-unsubstituted indoles, but also has provided an atom-economic and straightforward method for the synthesis of C3-allylic indoles with high regio- and enantioselectivity.
引用
收藏
页码:212 / 223
页数:13
相关论文
共 50 条
  • [31] SYNTHESIS AND RADICAL INDUCED RING-OPENING REACTION OF 1-TRIALKYLSILYL-2-VINYLCYCLOPROPANES
    MIURA, K
    OSHIMA, K
    UTIMOTO, K
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1990, 63 (06) : 1665 - 1677
  • [32] Rhodium-Catalyzed Chemodivergent Regio- and Enantioselective Allylic Alkylation of Indoles
    Sun, Minghe
    Liu, Min
    Li, Changkun
    CHEMISTRY-A EUROPEAN JOURNAL, 2021, 27 (10) : 3457 - 3462
  • [33] Iridium-Catalyzed Regio- and Enantioselective N-Allylation of Indoles
    Stanley, Levi M.
    Hartwig, John E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (42) : 7841 - 7844
  • [34] Regio- and Atroposelective Ring-Opening of 1H-Benzo[4,5]oxazolopyridinones
    Deng, Ruixian
    Dong, Puyang
    Ge, Jimeng
    Zhang, Wenjing
    Xue, Xiaoping
    Duan, Longhui
    Shi, Linlin
    Gu, Zhenhua
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2024, 63 (17)
  • [35] Regio- and stereoselective ring-opening cross-metathesis. Rapid entry into functionalized bicyclo[6.3.0] ring systems
    Snapper, ML
    Tallarico, JA
    Randall, ML
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (06) : 1478 - 1479
  • [36] A highly regio- and stereoselective nickel-catalyzed ring-opening reaction of alkyl- and allylzirconium reagents to 7-oxabenzonorbornadienes
    Wu, MS
    Jeganmohan, M
    Cheng, CH
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (23): : 9545 - 9550
  • [37] SUBSTITUENT EFFECTS IN REGIO- AND STEREOSELECTIVE RING-OPENING REACTION OF AZIRIDINES WITH Et3N.3HF FOR β-FLUOROAMINE SYNTHESIS
    Sasaki, Shigeru
    Watanabe, Satono
    Shiino, Kaori
    Yanaka, Yuko
    Kaneko, Shiho
    Miyamoto, Kana
    Yasui, Ayano
    Sakaino, Hina
    Teramoto, Hiroyoshi
    Yamauchi, Takayasu
    Higashiyama, Kimio
    HETEROCYCLES, 2018, 97 (02) : 823 - 841
  • [38] Organocatalyzed Photoredox Radical Ring-Opening Polymerization of Functionalized Vinylcyclopropanes
    Chen, Dian-Feng
    Bernsten, Simone
    Miyake, Garret M.
    MACROMOLECULES, 2020, 53 (19) : 8352 - 8359
  • [39] Enantioselective fluoride ring opening of aziridines enabled by cooperative Lewis acid catalysis
    Kalow, Julia A.
    Doyle, Abigail G.
    TETRAHEDRON, 2013, 69 (27-28) : 5702 - 5709
  • [40] Regio- and stereoselective ring opening of aziridines with nitric oxide
    Liu, ZQ
    Fan, Y
    Li, R
    Zhou, B
    Wu, LM
    TETRAHEDRON LETTERS, 2005, 46 (06) : 1023 - 1025