Stereoselective synthesis of highly congested tetralin-fused spirooxindoles with hydroxy group: Pseudo oxygen atom induced hydride shift/cyclization process

被引：7
作者：
Sakai, Dan [1 ]
Machida, Mizuki [1 ]
Mori, Keiji [1 ]
机构：
[1] Tokyo Univ Agr & Technol, Grad Sch Engn, Dept Appl Chem, 2-24-16 Nakacho, Koganei, Tokyo 1848588, Japan
来源：
TETRAHEDRON LETTERS | 2021年 / 83卷
基金：
日本学术振兴会;
关键词：
Tetralin; Spirooxindole; Hydride shift/cyclization process; C(sp(3))H bond functionalization; H BOND FUNCTIONALIZATION; ASYMMETRIC-SYNTHESIS; 1,5-HYDRIDE TRANSFER/CYCLIZATION; DIASTEREOSELECTIVE SYNTHESIS; EXPEDITIOUS SYNTHESIS; NATURAL-PRODUCTS; INTRAMOLECULAR CYCLIZATION; RAPID ACCESS; CONSTRUCTION; RING;
D O I：
10.1016/j.tetlet.2021.153408
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A highly stereoselective synthesis of tetralin-fused spirooxindoles with two contiguous stereogenic centers was developed. In the present reaction, not only the [1,5]-hydride shift/cyclization process, but also the replacement of nitrogen atom by oxygen atom occurred smoothly to give target compounds with hydroxy group in good chemical yields with good to excellent diastereoselectivities (up to d.r. = >20:1). Investigation of the reaction mechanism suggested that this atom replacement event occurred via the iminium cation intermediates. (C) 2021 Elsevier Ltd. All rights reserved.
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页数：4
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  • [1] Recent advances in hydride transfer-involved C(sp3)-H activation reactions
    An, Xiao-De
    Xiao, Jian
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (06) : 1364 - 1383
  • [2] Strategies for the enantioselective synthesis of spirooxindoles
    Ball-Jones, Nicolas R.
    Badillo, Joseph J.
    Franz, Annaliese K.
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (27) : 5165 - 5181
  • [3] Asymmetric Tandem 1,5-Hydride Shift/Ring Closure for the Synthesis of Chiral Spirooxindole Tetrahydroquinolines
    Cao, Weidi
    Liu, Xiaohua
    Guo, Jing
    Lin, Lili
    Feng, Xiaoming
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (04) : 1632 - 1636
  • [4] Highly Enantioselective Synthesis of Tetrahydroquinolines via Cobalt(II)-Catalyzed Tandem 1,5-Hydride Transfer/Cyclization
    Cao, Weidi
    Liu, Xiaohua
    Wang, Wentao
    Lin, Lili
    Feng, Xiaoming
    [J]. ORGANIC LETTERS, 2011, 13 (04) : 600 - 603
  • [5] Construction of Oxadiazepines via Lewis Acid-Catalyzed Tandem 1,5-Hydride Shift/Cyclization
    Chang, Yong-Zhi
    Li, Ming-Lei
    Zhao, Wen-Feng
    Wen, Xiaoan
    Sun, Hongbin
    Xu, Qing-Long
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (19) : 9620 - 9627
  • [6] Metal-Free Oxidation/C(sp3)-H Functionalization of Unactivated Alkynes Using Pyridine-N-Oxide as the External Oxidant
    Chen, Dian-Feng
    Han, Zhi-Yong
    He, Yu-Ping
    Yu, Jie
    Gong, Liu-Zhu
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (49) : 12307 - 12310
  • [7] Catalytic Enantioselective tert-Aminocyclization by Asymmetric Binary Acid Catalysis (ABC): Stereospecific 1,5-Hydrogen Transfer
    Chen, Liujuan
    Zhang, Long
    Lv, Jian
    Cheng, Jin-Pei
    Luo, Sanzhong
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (29) : 8891 - 8895
  • [8] Organocatalytic Asymmetric Assembly Reactions: Synthesis of Spirooxindoles via Organocascade Strategies
    Cheng, Daojuan
    Ishihara, Yoshihiro
    Tan, Bin
    Barbas, Carlos F., III
    [J]. ACS CATALYSIS, 2014, 4 (03): : 743 - 762
  • [9] Hydride transfer enabled switchable dearomatization of indoles in the carbocyclic ring and the pyrrole ring
    Duan, Kang
    Shi, Hongjin
    Wang, Lin-Xuan
    Li, Shuai-Shuai
    Xu, Lubin
    Xiao, Jian
    [J]. ORGANIC CHEMISTRY FRONTIERS, 2020, 7 (17) : 2511 - 2517
  • [10] Hydride Transfer Initiated Redox-Neutral Cascade Cyclizations of Aurones: Facile Access to [6,5] Spirocycles
    Duan, Kang
    An, Xiao-De
    Li, Long-Fei
    Sun, Lian-Lian
    Qiu, Bin
    Li, Xian-Jiang
    Xiao, Jian
    [J]. ORGANIC LETTERS, 2020, 22 (07) : 2537 - 2541
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