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
  • [21] Synthesis of substituted cyclopentenones via [4+1] annulation reactions of (trialkylsilyl)vinylketenes.
    Davie, CP
    Danheiser, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2003, 226 : U162 - U162
  • [22] Synthesis of Heterocyclic-Fused Furans and Dihydrofurans via (4+1)-Annulation with Ylide: Exploration of Unique Reactivity Behavior of α-Carbonyl Sulfoxonium Ylide
    Kumar, Gulshan
    Nagpure, Mithilesh
    Rao, Vajja Krishna
    Guchhait, Sankar K.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2022, 2022 (16)
  • [23] Synthesis of 2-indanones via [4+1] annulation reactions of (trialkylsilyl)arylketenes.
    Davie, CP
    Zhang, YJ
    Dalton, AM
    Danheiser, RL
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U112 - U113
  • [24] A Phosphorus(III)-Mediated (4+1)-Cycloaddition of 1,2-Dicarbonyls and Aza-o-Quinone Methides to Access 2,3-Dihydroindoles
    Eckert, Kaitlyn E.
    Lepore, Antonio J.
    Ashfeld, Brandon L.
    HELVETICA CHIMICA ACTA, 2019, 102 (12)
  • [25] Formal [4+1] cycloaddition of camphor-derived sulfonium salts with aldimines: enantioselective synthesis of 2,3-dihydrobenzofurans
    Cheng, Ying
    Hu, Xiao-Qiang
    Gao, Shuang
    Lu, Liang-Qiu
    Chen, Jia-Rong
    Xiao, Wen-Jing
    TETRAHEDRON, 2013, 69 (19) : 3810 - 3816
  • [26] Recent advances in the application of ylide-like species in [4+1]-annulation reactions: an updated review
    Ushakov, Pavel Yu
    Loffe, Sema L.
    Sukhorukov, Alexey Yu
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5358 - 5382
  • [27] SYNTHESIS OF 3-PYRROLINES VIA A [4+1]-ANNULATION STRATEGY
    PADWA, A
    NORMAN, BH
    TETRAHEDRON LETTERS, 1988, 29 (25) : 3041 - 3044
  • [28] Synthesis of Benzoxazoles via an Amine-Catalyzed [4+1] Annulation
    Song, Aiguo
    Chen, Xiaobei
    Song, Xixi
    Zhang, Xinshuai
    Zhang, Shilei
    Wang, Wei
    ORGANIC LETTERS, 2013, 15 (10) : 2510 - 2513
  • [29] Synthesis of Isoxazolines from Nitroalkanes via a [4+1]-Annulation Strategy
    Ushakov, Pavel Yu
    Khatuntseva, Elizaveta A.
    Nelyubina, Yulia, V
    Tabolin, Andrey A.
    Ioffe, Sema L.
    Sukhorukov, Alexey Yu
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (23) : 5322 - 5327
  • [30] Relay Visible-Light Photoredox Catalysis: Synthesis of Pyrazole Derivatives via Formal [4+1] Annulation and Aromatization
    Cheng, Jian
    Li, Weipeng
    Duan, Yingqian
    Cheng, Yixiang
    Yu, Shouyun
    Zhu, Chengjian
    ORGANIC LETTERS, 2017, 19 (01) : 214 - 217