Chiral Spirooxindole-Butenolide Synthesis through Asymmetric N-Heterocyclic Carbene-Catalyzed Formal (3+2) Annulation of 3-Bromoenals and Isatins

被引：65
|
作者：
Zheng, Chenguang [1 ]
Yao, Weijun [1 ]
Zhang, Yucheng [1 ]
Ma, Cheng [1 ]
机构：
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 19期
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; ALKYNYL ALDEHYDES; STEREOSELECTIVE-SYNTHESIS; GAMMA-BUTYROLACTONES; ALPHA; BETA-UNSATURATED ALDEHYDES; COOPERATIVE CATALYSIS; EFFICIENT SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; BENZOIN CONDENSATION; CONJUGATE UMPOLUNG;
D O I：
10.1021/ol502365r
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
By using an N-heterocyclic carbene catalyst bearing a hydroxyl moiety, the asymmetric formal (3 + 2) cyclization of aryl 3-bromoenals and isatins was achieved to produce a series of chiral spirooxindolebutenolides including an alkenyl-substituted compound, which underwent benzannulations with benzynes to form intriguing spirocyclic scaffolds.
引用
收藏
页码：5028 / 5031
页数：4
相关论文
共 50 条
  • [21] N-Heterocyclic Carbene-Catalyzed [3+3] Annulation of Indoline-2-thiones with Bromoenals: Synthesis of Indolo[2,3-b]dihydrothiopyranones
    Yi, Liang
    Chen, Kun-Quan
    Liang, Zhi-Qin
    Sun, De-Qun
    Ye, Song
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (01) : 44 - 48
  • [22] N-Heterocyclic Carbene-Catalyzed [3+4] Annulation of Enals and Alkenyl Thiazolones: Enantioselective Synthesis of Thiazole-Fused ε-Lactones
    Liang, Zhi-Qin
    Yi, Liang
    Chen, Kun-Quan
    Ye, Song
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (11) : 4841 - 4846
  • [23] N-Heterocyclic Carbene Catalyzed Enantioselective Annulation of Benzothiazolyl Ethyl Acetates with 2-Bromoenals
    Ni, Qijian
    Xiong, Jiawen
    Song, Xiaoxiao
    Raabe, Gerhard
    Enders, Dieter
    SYNLETT, 2015, 26 (11) : 1465 - 1469
  • [24] Effect of Temperature on N-Heterocyclic Carbene-Catalyzed [3+3] Annulation of α-Bromoenal with Enaminone
    Wang, Zhanlin
    Li, Ruyi
    Qian, Huimin
    Yao, Changsheng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2019, 39 (07) : 2075 - 2083
  • [25] N-Heterocyclic Carbene-Catalyzed Asymmetric Synthesis of Cyclopentenones
    Chen, Zhizhou
    Kong, Xiangwen
    Niu, Shengtong
    Yang, Shuang
    Liu, Jinggong
    Chen, Bolai
    Luo, Benlong
    Zhou, Changyu
    Ding, Chenglin
    Fang, Xinqiang
    ORGANIC LETTERS, 2021, 23 (09) : 3403 - 3408
  • [26] N-Heterocyclic carbene-catalyzed [3+3] annulation of bromoenals with 2-aminochromones to access chromeno[2,3-b]pyridinones
    Jiang, Pengrui
    Guo, Jingcheng
    Gong, Minghua
    Zhou, Xiangui
    Cao, Wei
    Fu, Zhenqian
    Huang, Wei
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2021, 19 (22) : 4882 - 4886
  • [27] N-heterocyclic carbene catalyzed [2+3] annulation reaction for the synthesis of trifluoroethyl 3,2′-spirooxindole γ-lactam
    Pu, Yiru
    Wang, Maolin
    Tian, Wanrong
    Ge, Xian
    Zhu, Dikai
    Wang, Chuanqi
    Zeng, Yingjie
    Tao, Feiyan
    Deng, Yun
    Lu, Jun
    RSC ADVANCES, 2024, 14 (26) : 18453 - 18458
  • [28] Theoretical study of the [3+4] annulation reaction of 2-bromoenals with malonates catalyzed by N-heterocyclic carbene
    Li, Zhilin
    Li, Yan
    Zhang, Zhiqiang
    MOLECULAR CATALYSIS, 2021, 509
  • [29] Diastereoselective synthesis of cyclopentanonef-used spirooxindoles by N-heterocyclic carbene-catalyzed homoenolate annulation with isatilidenes
    Patra, Atanu
    Bhunia, Anup
    Yetra, Santhivardhana Reddy
    Gonnade, Rajesh G.
    Biju, Akkattu T.
    ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (12): : 1584 - 1588
  • [30] Asymmetric N-Heterocyclic Carbene Catalyzed Annulation of 2-Alkenylbenzothiazoles with α-Chloro Aldehydes
    Song, Xiaoxiao
    Ni, Qijian
    Zhu, Chen
    Raabe, Gerhard
    Enders, Dieter
    SYNTHESIS-STUTTGART, 2015, 47 (03): : 421 - 428
12345