Base-mediated diastereoselective [4+3] annulation of in situ generated ortho-quinone methides with C, N-cyclic azomethine imines

被引：33
|
作者：
Xu, Jianfeng [1 ]
Yuan, Shiru [1 ]
Peng, Jingyi [1 ]
Miao, Maozhong [1 ]
Chen, Zhengkai [1 ]
Ren, Hongjun [1 ]
机构：
[1] Zhejiang Sci Tech Univ, Dept Chem, Hangzhou 310018, Zhejiang, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2017年 / 15卷 / 36期
基金：
中国国家自然科学基金;
关键词：
ENANTIOSELECTIVE 1,3-DIPOLAR CYCLOADDITION; ISATIN-DERIVED KETIMINES; BIOMIMETIC SYNTHESES; MELDRUMS ACID; CARBENE; ACCESS; CATALYST; YLIDES; ENALS;
D O I：
10.1039/c7ob01783a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient [4 + 3] annulation of 2-(1-tosylalkyl) phenols with C, N-cyclic azomethine imines via in situ generation of ortho-quinone methides (o-QMs) under mild basic reaction conditions is disclosed, furnishing biologically interesting seven-membered heterocyclic compounds with moderate to good yields and excellent diastereoselectivities. A gram-scale reaction is performed to demonstrate the potential in industrial application and two transition states are proposed to rationalize the outstanding diastereoselectivity.
引用
收藏
页码：7513 / 7517
页数：5
相关论文
共 29 条
  • [21] Highly Efficient Construction of Trifluoromethylated Heterocycles; [3+2] Annulation of N,N′-Cyclic or C,N-Cyclic Azomethine Imines with Trifluoromethyl-Containing Electron-Deficient Olefins
    Wang, De
    Deng, Hong-Ping
    Wei, Yin
    Xu, Qin
    Shi, Min
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (02) : 401 - 406
  • [22] Highly diastereoselective oxa-[3+3] cyclization with C,N-cyclic azomethine imines via the copper-catalyzed aerobic oxygenated C=C bond of indoles
    Yu, Lemao
    Zhong, Yuan
    Yu, Jicong
    Gan, Lu
    Cai, Zhengjun
    Wang, Rui
    Jiang, Xianxing
    CHEMICAL COMMUNICATIONS, 2018, 54 (19) : 2353 - 2356
  • [23] Diastereoselective synthesis of CF3-dihydrobenzofurans by [4+1] annulation of in situ-generated CF3-o-quinone methides and sulfur ylides
    Jha, Babli K.
    Prudhviraj, Jaggaraju
    Mainkar, Prathama S.
    Punna, Nagender
    Chandrasekhar, Srivari
    RSC ADVANCES, 2020, 10 (63) : 38588 - 38591
  • [24] (3+1) Annulation/Rearrangement Cascade of C,N-Cyclic Azomethine Imines and 3-Chlorooxindoles: Construction of Hexahydroindeno[2,1-c]pyrazole Spirooxindole Frameworks
    Zheng, Peng-Fei
    Zeng, Rong
    Jiang, Kun
    Li, Hong-Wei
    Ye, Ying
    Mu, Chao
    Shuai, Li
    Quyang, Qin
    Chen, Ying-Chun
    ORGANIC LETTERS, 2019, 21 (24) : 10052 - 10056
  • [25] A novel [4+3] annulation between isatin N,N '-cyclic azomethine 1,3-dipole and in situ generated nitrosoalkene for direct preparation of seven-membered heterocyclic spirooxindoles
    Li, Xia
    Li, Wen-Sheng
    Fu, Xiao
    Wan, Wen-Juan
    Wang, Li-Xin
    TETRAHEDRON LETTERS, 2024, 146
  • [26] Enantioselective Synthesis of Spiro Chroman-Isoindolinones via Formal (4+2) Cycloaddition of In Situ-Generated ortho-Quinone Methides with 3-Methylene Isoindolinones
    Wang, Tao
    Huang, Bo
    Wang, You-Qing
    ADVANCED SYNTHESIS & CATALYSIS, 2022, 364 (15) : 2596 - 2605
  • [27] B(C6F5)3-Catalyzed formal (4+1)-annulation of ortho-quinone methides with diazoacetates: access to 2,3-dihydrobenzofurans
    Xu, Guangyang
    Tang, Shengbiao
    Shao, Ying
    Sun, Jiangtao
    CHEMICAL COMMUNICATIONS, 2019, 55 (62) : 9096 - 9099
  • [28] Base-mediated formal [4+1] annulation of ortho- hydroxyphenyl substituted para- quinone methides and CF 3-imidoyl sulfoxonium ylides to access trifluoroacetimidoyl-substituted 2,3-dihydrobenzofurans
    Li, Chen
    Zhou, Mingshuo
    Chen, Zhengkai
    JOURNAL OF FLUORINE CHEMISTRY, 2024, 277
  • [29] Reaction of Push-Pull Enaminoketones and in Situ Generated ortho-Quinone Methides: Synthesis of 3-Acyl-4H-chromenes and 2-Acy1-1H-benzo[f]chromenes as Precursors for Hydroxybenzylated Heterocycles
    Lukashenko, Anton V.
    Osyanin, Vitaly A.
    Osipov, Dmitry V.
    Klimochkin, Yuri N.
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (03): : 1517 - 1528
123