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Synthesis 2021; 53(03): 518-526
DOI: 10.1055/s-0040-1707292
paper

Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and Allenoates

Teng Liu∗
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Chixian He
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Fan Wang
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Xiang Shen
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Yongqin Li
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Man Lang
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Guijun Li
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
,
Chao Huang∗
b   School of Chemistry and Environment, Yunnan Minzu University, Kunming, 650500, P. R. China   Email: huangchao@ynu.edu.cn
,
Feixiang Cheng∗
a   Center for Yunnan-Guizhou Plateau Chemical Functional ­Materials and Pollution Control, College of Chemistry and ­Environmental Science, Qujing Normal University, Qujing, 655011, P. R. China   Email: 15288404381@163.com   Email: fxcheng2019@163.com
› Author AffiliationsThis work was supported by the Program for the Applied Basic Research Foundation of Yunnan Province (No. 2018FB019), the Opening Foundation of Key Laboratory of Natural Resources and Pharmaceutical Chemistry, Ministry of Education, Yunnan University (No. 2018FH001-019), the NSFC (No. 21662046, 21202142), and Yunnan Local Colleges Research Projects of China (No. 2019FH001-006).
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Organocatalyzed [2+2] Cycloaddition Reactions between Quinone Imine Ketals and AllenoatesSynthesis 2021; 53(03): e1-e1
DOI: 10.1055/s-0041-1737548

Abstract

A new cycloaddition reaction of quinone imine ketals (QIKs), which could be utilized to the construction of functionalized azaspirocyclics under mild conditions, is described. This transformation involved a [2+2] cycloaddition reaction between QIKs and allenoates catalyzed by DABCO, and then treatment with 1 N HCl in one-pot. The strategy could provide a practical route to access azetidine-fused spirohexadienones in good to excellent yields and with high E-selectivity.

Key words

quinone imine ketals - allenoates - [2+2] cycloaddition - E-selectivity

Supporting Information



Publication History

Received: 29 July 2020

Accepted after revision: 28 August 2020

Article published online:
24 September 2020

© 2020. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Milan M, Salamone M, Costas M, Bietti M. Acc. Chem. Res. 2018; 51: 1984
      CrossrefPubMed
    • 1b Li J, Zhang Z, Wu L, Zhang W, Chen P, Lin Z, Liu G. Nature 2019; 574: 516
      CrossrefPubMed
    • 1c Lv J, Chen X, Xue X.-S, Zhao B, Liang Y, Wang M, Jin L, Yuan Y, Han Y, Zhao Y, Lu Y, Zhao J, Sun W.-Y, Houk KN, Shi Z. Nature 2019; 575: 336
      CrossrefPubMed
  • 2 Liu T. Chin. J. Org. Chem. 2020; 40 in press; DOI: 10.6023/cjoc202002033.
    Crossref
    • 3a Chou C.-T, Swenton JS. J. Am. Chem. Soc. 1987; 109: 6898
      Crossref
    • 3b Swenton JS, Bonke BR, Clark WM, Chen C.-P, Martin KV. J. Org. Chem. 1990; 55: 2027
      CrossrefPubMed
  • 4 Chuang KV, Navarro R, Reisman SE. Chem. Sci. 2011; 2: 1086
    CrossrefPubMed
    • 5a Hashimoto T, Nakatsu H, Takiguchi Y, Maruoka K. J. Am. Chem. Soc. 2013; 135: 16010
      PubMed
    • 5b Zhang Y.-C, Jiang F, Wang S.-L, Shi F, Tu S.-J. J. Org. Chem. 2014; 79: 6143
      CrossrefPubMed
    • 6a Zhang Y.-C, Zhao J.-J, Jiang F, Sun S.-B, Shi F. Angew. Chem. Int. Ed. 2014; 53: 13912
      PubMed
    • 6b Jiang F, Zhang Y.-C, Sun S.-B, Zhou L.-J, Shi F. Adv. Synth. Catal. 2015; 357: 1283
    • 6c Halder P, Humne VT, Mhaske SB. J. Org. Chem. 2019; 84: 1372
      PubMed
    • 6d Liu T, Liu J, Shen X, Xu J, Nian B, He N, Zeng S, Cheng F. Synthesis 2019; 51: 1365
    • 7a Song R, Han Z, He Q, Fan R. Org. Lett. 2016; 18: 5328
      PubMed
    • 7b Liu L, Chen K, Wu W.-Z, Wang P.-F, Song H.-Y, Sun H, Wen X, Xu Q.-L. Org. Lett. 2017; 19: 3823
      PubMed
    • 8a Shu C, Liao L.-H, Liao Y.-J, Hu X.-Y, Zhang Y.-H, Yuan W.-C, Zhang X.-M. Eur. J. Org. Chem. 2014; 21: 4467
    • 8b Liao L.-H, Zhang M.-M, Liao Y.-J, Yuan W.-C, Zhang X.-M. Synlett 2015; 26: 1720
      Article in Thieme Connect
    • 8c Li X, Li L, Wang W, He Q, Fan R. Org. Lett. 2020; 22: 823
      PubMed
    • 9a Kerr MA. Synlett 1995; 1165
    • 9b Banfield SC, England DB, Kerr MA. Org. Lett. 2001; 3: 3325
      PubMed
    • 9c Hashimoto T, Nakatsu H, Maruoka K. Angew. Chem. Int. Ed. 2015; 54: 4617
      PubMed
  • 10 Gu J, Xiao B.-X, Chen Y.-R, Du W, Chen Y.-C. Adv. Synth. Catal. 2016; 358: 196
  • 11 Liu T, Li Y, Cheng F, Shen X, Liu J, Lin J. Green Chem. 2019; 21: 3536
  • 12 Dalidowicz P, Swenton JS. J. Org. Chem. 1993; 58: 4802
    • 13a Antunes EM, Copp BR, Davies-Coleman MT, Samaai T. Nat. Prod. Rep. 2005; 22: 62
      PubMed
    • 13b Turiso FG.-L, de Curran DP. Org. Lett. 2005; 7: 151
      PubMed
    • 13c Lanza T, Leardini R, Minozzi M, Nanni D, Spagnolo P, Zanardi G. Angew. Chem. Int. Ed. 2008; 47: 9439
      PubMed
    • 13d Pirovani RV, Ferreira BR. V, Coelho F. Synlett 2009; 2333
    • 13e Reddy CR, Prajapti SK, Warudikar K, Ranjan R, Rao BB. Org. Biomol. Chem. 2017; 15: 3130 
      PubMed
    • 14a Lang G, Pinkert A, Blunt JW, Munro MH. G. J. Nat. Prod. 2005; 68: 1796
      PubMed
    • 14b Wang Q, Luo L, Wang J, Peng X, Hu C, Wang H. Org. Chem. Front. 2018; 5: 549
    • 14c Jia M.-Q, Liu C, You S.-L. J. Org. Chem. 2012; 77: 10996
      PubMed
    • 14d Unsworth WP, Cuthbertson JD, Taylor RJ. K. Org. Lett. 2013; 15: 3306
      PubMed
    • 14e Xu Z, Huang K, Liu T, Xie M, Zhang H. Chem. Commun. 2011; 47: 4923
      PubMed
    • 14f Liang J, Chen J, Du F, Zeng X, Li L, Zhang H. Org. Lett. 2009; 11: 2820
      PubMed
    • 15a Cheng Q, Wang Y, You S.-L. Angew. Chem. Int. Ed. 2016; 55: 3496
      PubMed
    • 15b Nakayama H, Harada S, Kono M, Nemoto T. J. Am. Chem. Soc. 2017; 139: 10188
      PubMed
    • 16a Li E.-Q, Huang Y. Chem. Commun. 2020; 56: 680
      PubMed
    • 16b Guo H, Fan YC, Sun Z, Wu Y, Kwon O. Chem. Rev. 2018; 118: 10049
      PubMed
    • 16c Ye L.-W, Zhou J, Tang Y. Chem. Soc. Rev. 2008; 37: 1140
      PubMed
    • 16d Xie P, Huang Y. Org. Biomol. Chem. 2015; 13: 8578
      PubMed
    • 16e Zhao Q, Hao W.-J, Shi H.-N, Xu T, Tu S.-J, Jiang B. Org. Lett. 2019; 21: 9784
      PubMed
    • 16f Ji C.-L, Hao W.-J, Zhang J, Geng F.-Z, Xu T, Tu S.-J, Jiang B. Org. Lett. 2019; 21: 6494
      PubMed
  • 17 Wei Y, Shi M. Acc. Chem. Res. 2010; 43: 1005
    PubMed
    • 18a Zhao G.-L, Huang J.-W, Shi M. Org. Lett. 2003; 5: 4737
      PubMed
    • 18b Zhao G.-L, Shi M. J. Org. Chem. 2005; 70: 9975
      PubMed
    • 18c Takizawa S, Arteaga FA, Yoshida Y, Suzuki M, Sasai H. Org. Lett. 2013; 15: 4142
      PubMed
    • 18d Zhang X.-C, Cao S.-H, Wei Y, Shi M. Chem. Commun. 2011; 47: 1548
      PubMed
    • 18e Chen X.-Y, Lin R.-C, Ye S. Chem. Commun. 2012; 48: 1317
      PubMed
    • 19a Denis J.-B, Masson G, Retailleau P, Zhu J. Angew. Chem. Int. Ed. 2011; 50: 5356
      PubMed
    • 19b Li E, Jin H, Jia P, Dong X, Huang Y. Angew. Chem. Int. Ed. 2016; 55: 11591
      PubMed
    • 19c Huang Z, Bao Y, Zhang Y, Yang F, Lu T, Zhou Q. J. Org. Chem. 2017; 82: 12726
      PubMed
    • 19d Mao B, Shi W, Liao J, Liu H, Zhang C, Guo H. Org. Lett. 2017; 19: 6340
      PubMed
    • 19e Kong X, Liu L, Luo S, Fan S, Qian H, Xiao H. Synlett 2018; 29: 1244
    • 19f Huang Z, Dai Z, Zhu J, Yang F, Zhou Q. Org. Biomol. Chem. 2018; 16: 6638
      PubMed
    • 19g Yu Z, Jin Z, Duan M, Bai R, Lu Y, Lan Y. J. Org. Chem. 2018; 83: 9740
    • 19h Dai Z, Zhu J, Wang J, Su W, Yang F, Zhou Q. Adv. Synth. Catal. 2020; 362: 545
      Crossref
    • 19i Dai Z, Zhu J, Su W, Zeng W, Liu Z, Chen M, Zhou Q. Org. Lett. 2020; 22 in press; DOI: 10.1021/acs.orglett.0c02558.
      CrossrefPubMed
    • 19j Lu D, Wu J.-H, Pan J, Chen X, Ren X, Wang T. Chem. Commun. 2020; 56 in press; DOI: 10.1039/D0CC04820H.
      CrossrefPubMed
  • 20 Hashimoto T, Sakata K, Tamakuni F, Dutton MJ, Maruoka K. Nat. Chem. 2013; 5: 240
    PubMed
  • 21 CCDC 1975357 and 1975358 contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
  • 22 Wang G, Liu X, Chen Y, Yang J, Li J, Lin L, Feng X. ACS Catal. 2016; 6: 2482
    CrossrefPubMed