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Synthesis 2022; 54(20): 4622-4628
DOI: 10.1055/a-1882-8128
DOI: 10.1055/a-1882-8128
paper
Access to Hexahydroindeno[2,1-c]pyran-Based Propellanes by a Domino Prins/Friedel–Crafts Cyclization
Y.N. thanks the Ministère de l’Enseignement supérieur, de la Recherche et de l’Innovation (MESRI) for a Ph.D. grant (2019–2021). The Centre National de la Recherche Scientifique (CNRS) and the Université Claude Bernard Lyon 1 are warmly thanked for financial support.

Abstract
Starting from readily available cyclic homoallylic alcohols, a Prins reaction allowed the formation of a bicyclic tetrahydropyranyl carbocation intermediate that is only trapped by electron-rich aromatic rings according a further intramolecular Friedel–Crafts reaction leading to new [4.4.3]propellane structures.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1882-8128.
- Supporting Information
Publikationsverlauf
Eingereicht: 26. April 2022
Angenommen nach Revision: 23. Juni 2022
Accepted Manuscript online:
23. Juni 2022
Artikel online veröffentlicht:
27. Juli 2022
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References
- 1 Nising CF, Bräse S. Chem Soc. Rev. 2012; 41: 988
- 2 Zhang Z, Tong R. Synthesis 2017; 49: 4899
- 3 Wang Y, Du D.-M. Org. Chem. Front. 2020; 7: 3266
- 4 Ahmad T, Ullah N. Org. Chem. Front. 2021; 8: 1329
- 5 Nasir NM, Ermanis K, Clarke PA. Org. Biomol. Chem. 2014; 12: 3323
- 6 Laina-Martin V, Fernandez-Salas JA, Aleman J. Chem. Eur. J. 2021; 27: 12509
- 7 Olier C, Kaafarani M, Gastaldi S, Bertrand MP. Tetrahedron 2010; 66: 413
- 8 Pastor IM, Yus M. Curr. Org. Chem. 2012; 16: 1277
- 9 Padmaja P, Narayana Reddy P, Subba Reddy BV. Org. Biomol. Chem. 2020; 18: 7514
- 10 Budakoti A, Mondal PK, Verma P, Khamrai J. Beilstein J. Org. Chem. 2021; 17: 932
- 11 Alder RW, Harvey JN, Oakley MT. J. Am. Chem. Soc. 2002; 124: 4960
- 12 Barry CS, Bushby N, Harding JR, Hughes RA, Parker GD, Roe R, Willis CL. Chem. Commun. 2005; 3727
- 13 Jasti R, Rychnovsky SD. Org. Lett. 2006; 8: 2175
- 14 Lalli C, van de Weghe P. Chem. Commun. 2014; 50: 7495
- 15 Liu L, Kaib PS. J, Tap A, List B. J. Am. Chem. Soc. 2016; 138: 10822
- 16 Sun H.-R, Zhao Q, Yang H, Yang S, Gou B.-B, Chen J, Zhou L. Org. Lett. 2019; 21: 7143
- 17 Uraguchi D, Ueoka F, Tanaka N, Kizu T, Takahashi W, Ooi T. Angew. Chem. Int. Ed. 2020; 59: 11456
- 18 Diac AP, Tepes A.-M, Soran A, Grosu I, Terec A, Roncali J, Bogdan E. Beilstein J. Org. Chem. 2016; 12: 825
- 19 Huang S, Ou W, Li W, Xiao H, Pang Y, Zhou Y, Wang X, Yang X, Wang L. Tetrahedron Lett. 2020; 61: 152052
- 20 Xu D, Liu J, Han X, Huang S, Yang X. Synth. Commun. 2022; 52: 724
- 21 Ondeyka JG, Helms GL, Hensens OD, Goetz MA, Zink DL, Tsipouras A, Shoop WL, Slayton L, Dombrowski AW, Polishook JD, Ostlind DA, Tsou NN, Ball RG, Singh SB. J. Am. Chem. Soc. 1997; 119: 8809
- 22 Smith AB. III, Davulcu AH, Cho YS, Ohmoto K, Kürti L, Ishiyama H. J. Org. Chem. 2007; 72: 4596
- 23 Roy S. Curr. Org. Chem. 2021; 25: 635
- 24 Rapelli C, Sridhar B, Reddy BV. Org. Biomol. Chem. 2020; 18: 6710
- 25 Barakov R, Shcherban N, Yaremov P, Bezverkhyy I, Cejka J, Opanasenko M. Green Chem. 2020; 22: 6992
- 26 Zheng J, Meng S, Wang Q. Beilstein J. Org. Chem. 2021; 17: 1481
- 27 Satteyyanaidu V, Chandrashekhar R, Reddy BV. S, Lalli C. Eur. J. Org. Chem. 2021; 138
- 28 Sidorenko AY, Kurban YM, Kravtsova AV, Il’ina IV, Li-Zhulanov NS, Sanchez-Velandia JE, Ahon A, Volcho KP, Salakthutdinov NF, Murzin DY, Agabekov VE. Appl. Catal., A 2022; 629: 118395
- 29 Barakov R, Shcherban N, Petrov O, Lang J, Shamzhy M, Opanasenko M, Cejka J. Inorg. Chem. Front. 2022; 9: 1244
- 30 Reddy BV. S, Reddy GN, Reddy MR, Lakshmi JK, Jagadeesh B, Sridhar B. Asian J. Org. Chem. 2015; 4: 1266
- 31 Reddy BV. S, Raju NP, Someswarao B, Reddy BJ. M, Sridhar B, Marumudi K, Kunwar AC. Org. Biomol. Chem. 2015; 13: 4733
- 32 Clarisse D, Pelotier B, Piva O, Fache F. Chem. Commun. 2012; 48: 157
- 33 Glachet T, Fache F, Pelotier B, Piva O. Synthesis 2017; 49: 5197
- 34 Segovia C, Fache F, Pelotier B, Piva O. ChemistrySelect 2019; 4: 3191
- 35 Nassar Y, Piva O. Org. Biomol. Chem. 2020; 18: 5811
- 36 Nassar Y, Piva O. Org. Biomol. Chem. 2021; 19: 9251
- 37 Ranu BC, Bhar S. J. Chem. Soc., Perkin Trans. 1 1992; 365
- 38 Hodgson A, Marshall J, Hallett P, Gallagher T. J. Chem. Soc., Perkin Trans. 1 1992; 2169
- 39 Crich D, Mo X.-S. J. Am. Chem. Soc. 1998; 120: 8298