Diastereoselective synthesis of trans-2,3-dihydroindoles via formal [4+1] annulation reactions of a sulfonium ylide

被引:3
|
作者
Jain, Anshul [1 ]
Kumari, Akanksha [1 ]
Metre, Ramesh K. [1 ]
Rana, Nirmal K. [1 ]
机构
[1] Indian Inst Technol Jodhpur, Dept Chem, Jodhpur 342030, India
关键词
CONSTRUCTION; INDOLINES;
D O I
10.1039/d3ob01793a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have established an in situ generated sulfonium-ylide mediated annulation to construct 2,3-disubstituted-2,3-dihydroindoles. The [4 + 1] annulation approach relied on Michael addition/substitution reactions. These reactions were carried out at ambient temperature to deliver dihydroindoles with excellent yields and diastereoselectivities. Moreover, the versatility of this approach allows for the introduction of various functional groups, enabling further diversification of the dihydroindoles. Also, the cascade approach was broadened to synthesize dihydrobenzofurans.
引用
收藏
页码:621 / 632
页数:12
相关论文
共 50 条
  • [31] Formal [4+1] annulation of fluorinated sulfonium salt with cyclic unsaturated imines to access CF3-substituted pyrroles
    Chen, Tao
    Wang, Aoning
    Zhang, Linxue
    Wei, Chenlong
    Huang, Juhui
    Liu, Xiang
    Fu, Zhenqian
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (14) : 3128 - 3133
  • [32] A cascade oxidation/[4+1] annulation of sulfonium salts for synthesis of polyfunctional furans: DMSO as one carbon source
    Shu, Wen-Ming
    Wang, Shuai
    Zhang, Xun-Fang
    He, Jian-Xin
    Wu, An-Xin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2019, 17 (17) : 4311 - 4316
  • [33] Palladium-Catalyzed (4+1) Annulation of 4-Vinylbenzodioxinones with Sulfur Ylides: Diastereoselective Synthesis of Dihydrobenzofuran Derivatives
    Tang, Yi
    Sun, Xiaojing
    Tan, Yu
    Wang, Lan
    Xiong, Yanmei
    Guo, Hongchao
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (12): : 8951 - 8959
  • [34] Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
    Tang, Xiang-Ying
    Zhang, Yong-Sheng
    He, Lv
    Wei, Yin
    Shi, Min
    CHEMICAL COMMUNICATIONS, 2015, 51 (01) : 133 - 136
  • [35] Sulfur Ylide Initiated [4+1]/[4+2] Annulation Reactions: A One-Pot Approach to Dibenzofuran Acrylate Derivatives
    Shao, Jiaan
    Chen, Wenteng
    Ying, Zhimin
    Liu, Shuangrong
    Luo, Feng
    Ou, Lili
    ORGANIC LETTERS, 2019, 21 (16) : 6370 - 6373
  • [36] A facile approach to spiro[dihydrofuran-2,3'-oxindoles] via formal [4+1] annulation reaction of fused 1H-pyrrole-2,3-diones with diazooxindoles
    Topanov, Pavel A.
    Maslivets, Anna A.
    Dmitriev, Maksim V.
    Mashevskaya, Irina V.
    Shklyaev, Yurii V.
    Maslivets, Andrey N.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2022, 18 : 1532 - 1538
  • [37] Study on the highly diastereoselective synthesis and structure of trans-2,3-diaryl substituted 1-aminocyclopropanecarboxylic acid derivatives
    Su, GF
    Pan, CX
    Mu, HT
    Zeng, LM
    Yu, KB
    ACTA CHIMICA SINICA, 2004, 62 (19) : 1941 - 1947
  • [38] Synthesis of 5-(Trifluoromethyl)pyrazolines by Formal [4+1]-Annulation of Fluorinated Sulfur Ylides and Azoalkenes
    Wang, Zhiyong
    Yang, Yanzhou
    Gao, Fang
    Wang, ZZhiyong
    Luo, Qian
    Fang, Ling
    ORGANIC LETTERS, 2018, 20 (04) : 934 - 937
  • [39] Rhodium(III)-catalyzed selective access to isoindolinones via formal [4+1] annulation of arylamides and propargyl alcohols
    Xu, Youwei
    Wang, Fen
    Yu, Songjie
    Li, Xingwei
    CHINESE JOURNAL OF CATALYSIS, 2017, 38 (08) : 1390 - 1398
  • [40] DIASTEREOSELECTIVE SYNTHESIS OF CIS-2,3-SUBSTITUTED OR TRANS-2,3-SUBSTITUTED TETRAHYDROFURANS AND 3,4-SUBSTITUTED 4-BUTANOLIDES
    FRAUENRATH, H
    PHILIPPS, T
    LIEBIGS ANNALEN DER CHEMIE, 1985, (10): : 1951 - 1961