Organocatalytic Asymmetric (4+3) Cycloaddition toward Optically Active Cyclohepta Fused Diindoles

被引:0
|
作者
Rui, Kanghua [1 ]
Shen, Hanxiao [1 ]
Lin, Xufeng [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310058, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 19期
基金
中国国家自然科学基金;
关键词
DIELS-ALDER REACTION; BISINDOLE;
D O I
10.1021/acs.joc.4c01772
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel asymmetric (4 + 3) cycloaddition of indole-2,3-quinodimethanes in situ generated from 3-methyl-2-indolylmethanols with 3-indolylmethanols via chiral phosphoric acid catalysis has been established. The cycloaddition reaction exhibits a broad substrate scope affording the diverse enantioenriched cyclohepta fused diindoles in high yields with good enantioselectivities. Significantly, this work represents the first application of 3-methyl-2-indolylmethanols as 4C synthons instead of the commonly reported three-atom synthons in cycloaddition reactions.
引用
收藏
页码:14348 / 14360
页数:13
相关论文
共 50 条
  • [41] A 4+3 cycloaddition approach to the synthesis of (±)-sterpurene
    Harmata, M
    Bohnert, GJ
    ORGANIC LETTERS, 2003, 5 (01) : 59 - 61
  • [42] IRON MEDIATED [4+3] CYCLOADDITION REACTIONS
    GIERING, WP
    BELMONTE, JE
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1981, 181 (MAR): : 106 - INOR
  • [43] Palladium-catalyzed asymmetric [4+3] cycloaddition of acyclic α,β-unsaturated imines with trimethylenemethane donors: access to chiral non-fused azepines
    Li, Ting-Peng
    Su, Shuixiu
    Shen, Jia-Huan
    Zang, Meng
    Liu, Yang-Zi
    Wang, Quannan
    Deng, Wei-Ping
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (08) : 2326 - 2331
  • [44] Organocatalytic Asymmetric [4+2] Cycloaddition of 1-Acetylcyclopentene and 1-Acetylcyclohexene for the Synthesis of Fused Carbocycles
    Nath, Utpal
    Pan, Subhas Chandra
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (43) : 6457 - 6461
  • [45] Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[b]-indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition
    Gelis, Coralie
    Levitre, Guillaume
    Merad, Jeremy
    Retailleau, Pascal
    Neuville, Luc
    Masson, Geraldine
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (37) : 12121 - 12125
  • [46] An Approach to Cyclohepta[b]indoles through an Allenamide (4+3) Cycloaddition-Grignard Cyclization-Chugaev Elimination Sequence
    He, Shuzhong
    Hsung, Richard P.
    Presser, William R.
    Ma, Zhi-Xiong
    Haugen, Bryan J.
    ORGANIC LETTERS, 2014, 16 (08) : 2180 - 2183
  • [47] Concise Formal Synthesis of (+)-Englerin A and Total Synthesis of (-)-Orientalol F: Establishment of the Stereochemistry of the Organocatalytic [4+3]-Cycloaddition Reaction
    Wang, Chao-Lei
    Sun, Bing-Feng
    Chen, Shu-Guang
    Ding, Rui
    Lin, Guo-Qiang
    Xu, Jin-Yi
    Shang, Yong-Jia
    SYNLETT, 2012, (02) : 263 - 266
  • [48] Stereoselective synthesis of (±)-urechitol A employing [4+3] cycloaddition
    Sumiya, Tatsunobu
    Ishigami, Ken
    Watanabe, Hidenori
    TETRAHEDRON, 2016, 72 (44) : 6982 - 6987
  • [49] RELATIVE STEREOCONTROL IN AN INTRAMOLECULAR 4+3 CYCLOADDITION REACTION
    HARMATA, M
    GAMLATH, CB
    BARNES, CL
    TETRAHEDRON LETTERS, 1993, 34 (02) : 265 - 268
  • [50] 4+3 cycloaddition approach to the synthesis of spatol.
    Harmata, M
    Rashatasakhon, P
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U142 - U143