Synthesis 2020; 52(04): 553-564
DOI: 10.1055/s-0039-1690745
paper
© Georg Thieme Verlag Stuttgart · New York

Formal [8+3]-Annulation between Azaoxyallyl Cations and Tropones

Guillaume Force
a   Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France   Email: vincent.gandon@u-psud.fr   Email: david.leboeuf@u-psud.fr
,
Amélie Pérot
b   Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France
,
Régis Guillot
a   Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France   Email: vincent.gandon@u-psud.fr   Email: david.leboeuf@u-psud.fr
,
a   Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France   Email: vincent.gandon@u-psud.fr   Email: david.leboeuf@u-psud.fr
b   Laboratoire de Chimie Moléculaire (LCM), CNRS UMR 9168, Ecole Polytechnique, Institut Polytechnique de Paris, route de Saclay, 91128 Palaiseau cedex, France
,
David Leboeuf
a   Institut de Chimie Moléculaire et des Matériaux d’Orsay (ICMMO), CNRS UMR 8182, Université Paris-Sud, Université Paris-Saclay, Bâtiment 420, 91405 Orsay cedex, France   Email: vincent.gandon@u-psud.fr   Email: david.leboeuf@u-psud.fr
› Author Affiliations
We gratefully thank the Agence Nationale de la Recherche (ANR-16-CE07-0022 funding for G.F.).
Further Information

Publication History

Received: 03 September 2019

Accepted after revision: 25 October 2019

Publication Date:
11 November 2019 (online)


Published as part of the Bürgenstock Special Section 2019 Future Stars in Organic Chemistry

Abstract

For the first time, azaoxyallyl cations were used as cycloaddition partners with tropone derivatives to access nitrogen-containing [7,6]-fused bicycles in a metal-free process under mild reaction conditions. DFT computations have been used to shed light on the selectivities observed during the course of the reaction.

Supporting Information

 
  • References


    • For relevant reviews on tropone and related compounds, see:
    • 1a Bentley R. Nat. Prod. Rep. 2008; 25: 118
    • 1b Liu N, Song W, Schienebeck CM, Zhang M, Tang W. Tetrahedron 2014; 70: 9281
    • 1c Dastan A, Kilic H, Saracoglu N. Beilstein J. Org. Chem. 2018; 14: 1120
    • 1d Guo H, Roman D, Beemelmanns C. Nat. Prod. Rep. 2019; 36: 1137

      For recent examples of cycloadditions involving tropone derivatives, see:
    • 2a Nair V, Poonoth M, Vellalath S, Suresh E, Thirumalai R. J. Org. Chem. 2006; 71: 8964
    • 2b Trost BM, McDougall PJ, Hartmann O, Wathen PT. J. Am. Chem. Soc. 2008; 130: 14960
    • 2c Li P, Yamamoto H. J. Am. Chem. Soc. 2009; 131: 16628
    • 2d Ashenhurst JA, Isakovic L, Gleason JL. Tetrahedron 2010; 66: 368
    • 2e Rivero AR, Fernández I, Sierra MA. Org. Lett. 2013; 15: 4928
    • 2f Tejero R, Ponce A, Adrio J, Carretero JC. Chem. Commun. 2013; 49: 10406
    • 2g Liu HL, Wu Y, Zhao Y, Li Z, Zhang L, Yang WJ, Jiang H, Jing CF, Yu H, Wang B, Xiao YM, Guo HC. J. Am. Chem. Soc. 2014; 136: 2625
    • 2h Teng H.-L, Yao L, Wang C.-J. J. Am. Chem. Soc. 2014; 136: 4075
    • 2i Kumar P, Thakur A, Hong X, Houk KN, Louie J. J. Am. Chem. Soc. 2014; 136: 17844
    • 2j Esteban F, Alfaro R, Yuste F, Parra A, Ruano JL, Alemán J. Eur. J. Org. Chem. 2014; 1395
    • 2k Thangaraj M, Bhojgude SS, Bisht RH, Gonnade RG, Biju AT. J. Org. Chem. 2014; 79: 4757
    • 2l Jia S, Su S, Li C, Jia X, Li J. Org. Lett. 2014; 16: 5604
    • 2m Mose R, Preegel G, Larsen J, Jakobsen S, Iversen EH, Jørgensen KA. Nat. Chem. 2017; 9: 487
    • 2n Yu P, Chen TQ, Yang Z, He CQ, Patel A, Lam Y.-h, Liu C.-Y, Houk KN. J. Am. Chem. Soc. 2017; 139: 8251
    • 2o Liu H, Jia H, Shi W, Wang C, Zhang C, Guo H. Org. Lett. 2018; 20: 3570
    • 2p Zhang J, Xiao W, Hu H, Lin L, Liu X, Feng X. Chem. Eur. J. 2018; 24: 13428
    • 2q Yu P, He CQ, Simon A, Li W, Mose R, Thøgersen MK, Jørgensen KA, Houk KN. J. Am. Chem. Soc. 2018; 140: 13726
    • 2r Xia F, Gao Z.-H, Zhangm C.-L, Ye S. Adv. Synth. Catal. 2019; 361: 2291
    • 2s Wang S, Rodríguez-Escrich C, Fianchini M, Maseras F, Pericàs MA. Org. Lett. 2019; 21: 3187

      For reviews on azaoxyallyl cations, see:
    • 3a Barnes KL, Koster AK, Jeffrey CS. Tetrahedron Lett. 2014; 55: 4690
    • 3b Xuan J, Cao X, Cheng X. Chem. Commun. 2018; 54: 5154

      For seminal works, see:
    • 4a Jeffrey CS, Barnes KL, Eickhoff JA, Carson CR. J. Am. Chem. Soc. 2011; 133: 7688
    • 4b DiPoto MC, Hughes RP, Wu J. J. Am. Chem. Soc. 2015; 137: 14861

    • For selected recent examples on the use of azaoxyallyl cations in synthesis, see:
    • 4c Zhang K, Yang C, Yao H, Lin A. Org. Lett. 2016; 18: 4618
    • 4d Acharya A, Montes K, Jeffrey CS. Org. Lett. 2016; 18: 6082
    • 4e Shao P.-L, Li Z.-R, Wang Z.-P, Zhou M.-H, Wu Q, Hu P, He Y. J. Org. Chem. 2017; 82: 10680
    • 4f DiPoto MC, Wu J. Org. Lett. 2018; 20: 499
    • 4g Zhang C, Ji W, Liu YA, Song C, Liao X. J. Nat. Prod. 2018; 81: 1065
    • 4h Xu X, Zhang K, Li P, Yao H, Lin A. Org. Lett. 2018; 20: 1781
    • 4i Ji D, Sun J. Org. Lett. 2018; 20: 2745
    • 4j Singh R, Nagesh K, Yugandhar D, Prasanthi AV. G. Org. Lett. 2018; 20: 4848
    • 4k Baldé B, Force G, Marin L, Guillot R, Schulz E, Gandon V, Lebœuf D. Org. Lett. 2018; 20: 7405
    • 4l Jaiswal V, Mondal B, Singh K, Das D, Saha J. Org. Lett. 2019; 21: 5848

      For recent reviews on HFIP, see:
    • 5a Sugiishi T, Matsugi M, Hamamoto H, Amii H. RSC Adv. 2015; 5: 17269
    • 5b Wencel-Delord J, Colobert F. Org. Chem. Front. 2016; 3: 394
    • 5c Colomer I, Chamberlain AE. R, Haughey MB, Donohoe TJ. Nat. Rev. Chem. 2017; 1: 0088
  • 6 Zhao Y, Truhlar DG. J. Chem. Phys. 2006; 125: 194101
    • 7a MacLean AD, Chandler GS. J. Chem. Phys. 1980; 72: 5639
    • 7b Krishnan R, Binkley JS, Seeger R, Pople JA. J. Chem. Phys. 1980; 72: 650
  • 8 Marenich AV, Cramer CJ, Truhlar DG. J. Phys. Chem. B 2009; 113: 6378
  • 9 Li G.-X, Morales-Rivera CA, Gao F, Wang Y, He G, Liu P, Chen G. Chem. Sci. 2017; 8: 7180
  • 10 When isolated, minor compound 4′a was subjected to the reaction conditions; only 30% conversion into 4a was observed after 24 h.
    • 11a Berkessel A, Adrio JA, Hüttenhain D, Neudörfl JM. J. Am. Chem. Soc. 2006; 128: 8421
    • 11b Berkessel A, Adrio JA. J. Am. Chem. Soc. 2006; 128: 13412