Download PDF
Synthesis 2021; 53(21): 4030-4041
DOI: 10.1055/a-1526-7839
feature

Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylates

Jiru Shao
a   Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200241, P. R. of China
,
Caiyun An
a   Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200241, P. R. of China
,
Sunewang R. Wang  ∗
a   Chang-Kung Chuang Institute, School of Chemistry and Molecular Engineering, East China Normal University, 500 Dongchuan Lu, Shanghai 200241, P. R. of China
b   Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, East China Normal University, 3663 North Zhongshan Lu, Shanghai 200062, P. R. of China
› Author AffiliationsThis work was sponsored by the Shanghai Pujiang Program (Grant No. 19PJ1402700), the Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning, the National Natural Science Foundation of China (No. 22071059), and the East China Normal University (ECNU).
› Further Information
    Permissions and Reprints All articles of this category


Corrected by:

Facile Synthesis of Polysubstituted 2-Pyrones via TfOH-Mediated Ring Expansion of 2-Acylcyclopropane-1-carboxylatesSynthesis 2021; 53(21): e5-e5
DOI: 10.1055/s-0040-1720012

Abstract

A facile route to polysubstituted 2-pyrones from readily available 2-acylcyclopropane-1-aryl-1-carboxylates mediated by TfOH is reported. The strongly donating 1-aryl group is important for directing the C–C bond cleavage of the donor-acceptor cyclopropane ring, which then leads to the formation of the 2-pyrone ring through lactonization.

Key words

carbocycles - heterocycles - ring expansion - Brønsted acid - synthetic methods - cyclopropanes - 2-pyrones

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1526-7839.
  • Supporting Information


Publication History

Received: 19 May 2021

Accepted after revision: 10 June 2021

Accepted Manuscript online:
10 June 2021

Article published online:
08 July 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

    • 1a Sunazuka T, Omura S. Chem. Rev. 2005; 105: 4559
      CrossrefPubMed
    • 1b Goel A, Ram VJ. Tetrahedron 2009; 65: 7865
      Crossref
    • 1c McGlacken GP, Fairlamb IJ. S. J. Nat. Prod. 2005; 22: 369
      CrossrefPubMed
    • 1d Stout EP, Hasemeyer AP, Lane AL, Davenport TM, Engel S, Hay ME, Fairchild CR, Prudhomme J, Le Roch K, Aalbersberg W, Kubanek J. Org. Lett. 2009; 11: 225
      CrossrefPubMed
    • 1e Praveen C, Ayyanar A, Perumal PT. Bioorg. Med. Chem. Lett. 2011; 21: 4170
      CrossrefPubMed
    • 1f Dong Y, Goto KN, Lai CY, Natschke SL. M, Bastow KF, Lee KH. Bioorg. Med. Chem. Lett. 2011; 21: 2341
      CrossrefPubMed
    • 1g Shankar R, Chakravarti B, Singh US, Ansari MI, Deshpande S, Dwivedi SK. D, Bid HK, Konwar R, Kharkwal G, Chandra V, Dwivedi A, Hajela K. Bioorg. Med. Chem. 2009; 17: 3847
      CrossrefPubMed
    • 1h Fairlamb IJ. S, Morrison LR, Dickinson JM, Lu FJ, Schmidt JP. Bioorg. Med. Chem. 2004; 12: 4285
      CrossrefPubMed
    • 1i Rao PN. P, Uddin MJ, Knaus EE. J. Med. Chem. 2004; 47: 3972
      CrossrefPubMed
    • 1j Marrison LR, Dickinson JM, Fairlamb LJ. Bioorg. Med. Chem. Lett. 2002; 12: 3509
      CrossrefPubMed
    • 1k Rao PN. P, Amini PM, Li H, Habeeb AG, Knaus EE. J. Med. Chem. 2003; 46: 4872
      CrossrefPubMed
    • 1l Lee I.-K, Yun B.-S. J. Antibiot. 2011; 64: 349
      CrossrefPubMed
    • 1m Lee JS. Mar. Drugs 2015; 13: 1581
    • 1n Fürstner A. Angew. Chem. Int. Ed. 2018; 57: 4215
      CrossrefPubMed

      For selective recent examples:
    • 2a Palani V, Perea MA, Gardner KE, Sarpong R. Chem. Sci. 2021; 12: 1528
      CrossrefPubMed
    • 2b Chinta BS, Lee D, Hoye TR. Org. Lett. 2021; 23: 2189
      CrossrefPubMed
    • 2c Cole CJ. F, Fuentes L, Snyder SA. Chem. Sci. 2020; 11: 2175
      CrossrefPubMed
    • 2d Zhang X, Beaudry CM. Org. Lett. 2020; 22: 6086
      CrossrefPubMed
    • 2e Disadee W, Lekky A, Ruchirawat S. J. Org. Chem. 2020; 85: 1802
      CrossrefPubMed
    • 2f Liang X.-W, Zhao Y, Si X.-G, Xu M.-M, Tan J.-H, Zhang Z.-M, Zheng C.-G, Zheng C, Cai Q. Angew. Chem. Int. Ed. 2019; 58: 14562
      CrossrefPubMed
    • 2g Cai Q. Chin. J. Chem. 2019; 37: 946
      Crossref

      For selective recent examples:
    • 3a Zheng P, Li C, Mou C, Pan D, Wu S, Xue W, Jin Z, Chi YR. Asian J. Org. Chem. 2019; 8: 1067
      Crossref
    • 3b Xu L.-C, Zhou P, Li J.-Z, Hao W.-J, Tu S.-J, Jiang B. Org. Chem. Front. 2018; 5: 753
      Crossref
    • 3c Kim HY, Oh K. Org. Lett. 2017; 19: 4904
      CrossrefPubMed
    • 3d Minakata S, Inada H, Komatsu M, Kajii H, Ohmori Y, Tsumura M, Namura K. Chem. Lett. 2008; 37: 248
      Crossref
    • 3e Usachev BI, Obydennov DL, Röschenthaler GV, Sosnovskikh VY. Org. Lett. 2008; 10: 2857
      CrossrefPubMed
    • 3f Zhu XF, Schaffner AP, Li RC, Kwon O. Org. Lett. 2005; 7: 2977
      CrossrefPubMed
    • 3g Katritzky AR, Wang Z, Wang M, Hall CD, Suzuki K. J. Org. Chem. 2005; 70: 4854
      CrossrefPubMed
    • 3h Ma S, Yu S, Yin S. J. Org. Chem. 2003; 68: 8996
      CrossrefPubMed
    • 3i Yao T, Larock RC. J. Org. Chem. 2003; 68: 5936
      CrossrefPubMed
    • 3j Ma S, Yin S, Li L, Tao F. Org. Lett. 2002; 4: 505
      CrossrefPubMed
    • 3k Hirano K, Minakata S, Komatsu M. Bull. Chem. Soc. Jpn. 2001; 74: 1567
      Crossref
    • 4a Zhou P, Yang W.-T, Rahman AU, Li G, Jiang B. J. Org. Chem. 2020; 85: 360
      CrossrefPubMed
    • 4b Matsuda T, Suzuki K. RSC Adv. 2014; 4: 37138
      Crossref
    • 4c Chaładaj W, Corbet M, Fürstner A. Angew. Chem. Int. Ed. 2012; 51: 6929
      CrossrefPubMed
    • 4d Bengtsson C, Almqvist F. J. Org. Chem. 2011; 76: 9187
    • 4e Mochida S, Hirano K, Satoh T, Miura M. J. Org. Chem. 2009; 74: 6295
      CrossrefPubMed
    • 4f Luo T, Schreiber SL. Angew. Chem. Int. Ed. 2007; 46: 8250
      CrossrefPubMed
    • 4g Fukuyama T, Higashibeppu Y, Yamaura R, Ryu I. Org. Lett. 2007; 9: 587
      CrossrefPubMed
    • 4h Wang Y, Burton DJ. J. Org. Chem. 2006; 71: 3859
      CrossrefPubMed
    • 4i Komiyama T, Takaguchi Y, Gubaidullin AT, Mamedov VA, Litvinov IA, Tsuboi S. Tetrahedron 2005; 61: 2541
      Crossref
    • 4j Louie J, Gibby JE, Farnworth MV, Tekavec TN. J. Am. Chem. Soc. 2002; 124: 15188
      CrossrefPubMed
    • 4k Thibonnet J, Abarbri M, Parrain JL, Duchêne A. J. Org. Chem. 2002; 67: 394
      CrossrefPubMed
    • 4l Liu R, Li X, Li X, Wang J, Yang Y. J. Org. Chem. 2019; 84: 14141
      CrossrefPubMed
    • 4m Preindl J, Schulthoff S, Wirtz C, Lingnau J, Fürstner A. Angew. Chem. Int. Ed. 2017; 56: 7525
      CrossrefPubMed
    • 4n Preindl J, Jouvin K, Laurich D, Seidel G, Fürstner A. Chem. Eur. J. 2016; 22: 237
      CrossrefPubMed
    • 4o Manikandan R, Jeganmohan M. Org. Lett. 2014; 16: 652
      CrossrefPubMed
    • 4p Anastasia LXu C.. Negishi E.-i. Tetrahedron Lett. 2002; 43: 5673
      Crossref
    • 4q Bellina F, Biagetti M, Carpita A, Rossi R. Tetrahedron Lett. 2001; 42: 2859
      Crossref
    • 5a Liu J, Liu R, Wei Y, Shi M. Trends Chem. 2019; 1: 779
    • 5b De N, Yoo EJ. ACS Catal. 2018; 8: 48
      Crossref
    • 5c Special Issue: Chemistry of Donor-Acceptor Cyclopropanes and Cyclobutanes: Reissig H.-U, Werz DB. Isr. J. Chem. 2016; 56: 365-577
      Crossref
    • 5d Grover HK, Emmett MR, Kerr MA. Org. Biomol. Chem. 2015; 13: 655
      CrossrefPubMed
    • 5e Novikov RA, Tomilov YV. Mendeleev Commun. 2015; 25: 1
      Crossref
    • 5f Schneider TF, Kaschel J, Werz DB. Angew. Chem. Int. Ed. 2014; 53: 5504
      CrossrefPubMed
    • 5g Cavitt MA, Phun KH, France S. Chem. Soc. Rev. 2014; 43: 804
      CrossrefPubMed
    • 5h De Nanteuil F, De Simone F, Frei R, Benfatti F, Serrano E, Waser J. Chem. Commun. 2014; 50: 10912
      CrossrefPubMed
    • 5i Reissig HU, Zimmer R. Chem. Rev. 2003; 103: 1151
      CrossrefPubMed
    • 5j Werz DB, Biju AT. Angew. Chem. Int. Ed. 2020; 59: 3385
      CrossrefPubMed
    • 5k Xia Y, Liu X, Feng X. Angew. Chem. Int. Ed. 2020; 60: 9192
      PubMed
    • 5l Pirenne V, Muriel B, Waser J. Chem. Rev. 2021; 121: 227
      CrossrefPubMed
    • 5m Augustin AU, Werz DB. Acc. Chem. Res. 2021; 54: 1528
      CrossrefPubMed
  • 6 Shao J, Luo Q, Bi H, Wang SR. Org. Lett. 2021; 23: 459
    CrossrefPubMed
    • 7a Li G.-Q, Dai L.-X, You S.-L. Org. Lett. 2009; 11: 1623
      CrossrefPubMed
    • 7b Sathishkannan G, Srinivasan K. Adv. Synth. Catal. 2014; 356: 729
      Crossref
    • 7c Zhu Y, Gong Y. J. Org. Chem. 2015; 80: 490
      CrossrefPubMed
    • 8a Yin D, Liu H, Lu C.-D, Xu Y.-J. J. Org. Chem. 2017; 82: 3252
      CrossrefPubMed
    • 8b Fauduet H, Burgada R. Synthesis 1980; 642
    • 8c Romanova IP, Bogdanov AV, Mironov VF, Shaikhutdinova GR, Larionova OA, Latypov SK, Bal-andina AA, Yakh-varov DG, Gubaidullin AT, Saifina AF, Sinyashin OG. J. Org. Chem. 2011; 76: 2548
      CrossrefPubMed
    • 8d Zhang J, Hao J, Huang Z, Han J, He Z. Chem. Commun. 2020; 56: 10251
      CrossrefPubMed
    • 9a Venkatesh C, Singh PP, Ila H, Junjappa H. Eur. J. Org. Chem. 2006; 5378
    • 9b Nguyen TN, Nguyen TS, May JA. Org. Lett. 2016; 18: 3786
      CrossrefPubMed
    • 10a Węcławski MK, Tasior M, Hammann T, Cywiński PJ, Gryko DT. Chem. Commun. 2014; 50: 9105
      CrossrefPubMed
    • 10b Węcławski MK, Deperasińska I, Banasiewicz M, Young DC, Leniak A, Gryko DT. Chem. Asian J. 2019; 14: 1763
      CrossrefPubMed
    • 10c Xue W, Wang D, Li C, Zhai Z, Wang T, Liang Y, Zhang Z. J. Org. Chem. 2020; 85: 3689
      CrossrefPubMed
    • 11a Campeau L.-C, Parisien M, Leblanc M, Fagnou K. J. Am. Chem. Soc. 2004; 126: 9186
      CrossrefPubMed
    • 11b Campeau L.-C, Parisien M, Jean A, Fagnou K. J. Am. Chem. Soc. 2006; 128: 581
      CrossrefPubMed
    • 12a Zhang J, Li S, Qiao Y, Peng C, Wang X.-N, Chang J. Chem. Commun. 2018; 54: 12455
      CrossrefPubMed
    • 12b Hsiao H.-C, Annamalai P, Jayakumar J, Sun S.-Y, Chuang S.-C. Adv. Synth. Catal. 2021; 363: 1695
      Crossref
  • 13 Armstrong A, Baxter CA, Lamont SG, Pape AR, Wincewicz R. Org. Lett. 2007; 9: 351
    CrossrefPubMed
    • 14a Minatti A, Zheng X, Buchwald SL. J. Org. Chem. 2007; 72: 9253
      CrossrefPubMed
    • 14b Komatsuki K, Kozuma A, Saito K, Yamada T. Org. Lett. 2019; 21: 6628
      CrossrefPubMed
  • 15 Tan P, Wang H, Wang SR. Org. Lett. 2021; 23: 2590
    CrossrefPubMed
  • 16 CCDC 2083287 (8n) contains 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/structures.