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DOI: 10.1055/s-0034-1380223
Cycloaddition Reactions of Propyne Iminium Salts and Enol Ethers
Publication History
Received: 18 May 2015
Accepted after revision: 20 June 2015
Publication Date:
04 August 2015 (online)
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Dedicated to Professor Manfred Regitz on the occasion of his 80th birthday
Abstract
Acetylenic iminium salts (propyne iminium salts) react with cyclic enol ethers in a thermal [2+2] cycloaddition reaction to afford condensed cyclobutene iminium salts. With acyclic enol ethers, a cycloaddition/electrocyclic ring-opening sequence occurs to give (1-alkoxybuta-1,3-dien-2-yl)methane iminium salts as mixtures of diastereoisomers. An analogous scenario is observed with 5-phenyl-2-vinylfuran as the nucleophilic olefinic component. With 1-methoxy-3-trimethylsilyloxy-1,3-butadiene, propyne iminium salts undergo a [4+2] cycloaddition. For all reactions, traces of acid must be quenched with solid K2CO3 or CaO to avoid immediate polymerization of the enol ether.
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References
- 1a Baldwin JE In Comprehensive Organic Synthesis . Vol. 5. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 63
- 1b Lee-Ruff E, Mladenova G. Chem. Rev. 2003; 103: 1449
- 2 Razin VV. Science of Synthesis. Vol. 47b; de Meijere A. Georg Thieme Verlag; Stuttgart: 2010: 883
- 3 Hoffmann R, Woodward RB. Angew. Chem., Int. Ed. Engl. 1969; 8: 781
- 4 Huisgen R. Acc. Chem. Res. 1977; 10: 117
- 5a Urrutia-Desmaison G, Huisgen R, Nöth H. Helv. Chim. Acta 2012; 95: 1
- 5b Huisgen R, Urrutia Desmaison G. Helv. Chim. Acta 2012; 95: 1049
- 6a Takasu K, Ueno M, Inanaga K, Ihara M. J. Org. Chem. 2004; 69: 517
- 6b Inanaga K, Takasu K, Ihara M. J. Am. Chem. Soc. 2005; 127: 3668
- 6c Inanaga K, Ogawa Y, Nagamoto Y, Daigaku A, Tokuyama H, Takemoto Y, Takasu K. Beilstein J. Org. Chem. 2012; 8: 658
- 6d Kurahasi K, Takemoto Y, Takasu K. ChemSusChem 2012; 5: 270
- 6e Hata K, Arichi N, Yamaoka Y, Yamada K, Takemoto Y, Takasu K. Asian J. Org. Chem. 2014; 3: 706
- 6f Arichi N, Hata K, Takemoto Y, Yamada K, Yamaoka Y, Takasu K. Tetrahedron 2015; 71: 233
- 7 Canales E, Corey EJ. J. Am. Chem. Soc. 2007; 129: 12686
- 8 Gollnick K, Fries S. Angew. Chem. 1980; 92: 848
- 9 Nicolaou KC, Hwang C.-K, Duggan ME, Bal Reddy K. Tetrahedron Lett. 1987; 28: 1501
- 10a Tsvetkov NP, Koldobskii AB, Godovikov IA, Kalinin VN. Dokl. Chem. 2005; 404 ( 02,) 210
- 10b Koldobskii AB, Tsvetkov NP, Godovikov IA, Kalinin VN. Russ. Chem. Bull., Int. Ed. 2009; 58: 1438
- 11 Koldobskii AB, Tsvetkov NP, Verteletskii PV, Godovikov IA, Kalinin VN. Russ. Chem. Bull., Int. Ed. 2009; 58: 1431
- 12 Miesch M, Wendling F. Eur. J. Org. Chem. 2000; 3381
- 13 Franck-Neumann M, Miesch M, Gross L. Tetrahedron Lett. 1992; 33: 3879
- 14 Ishihara K, Fushimi M. J. Am. Chem. Soc. 2008; 130: 7532
- 15 Yedulla VR, Pradhan P, Yang L, Lakshman M. Eur. J. Org. Chem. 2015; 750
- 16 Yoshida H, Ito Y, Yoshikawa Y, Ohshita J, Takaki K. Chem. Commun. 2011; 47: 8664
- 17 Murakami M In Comprehensive Organic Synthesis II . 2nd ed., Vol. 5; Knochel P, Molander G. Elsevier; Amsterdam: 2014: Chap. 5.16, 732
- 18 Maas G, Singer B, Wald P, Gimmy M. Chem. Ber. 1988; 121: 1847
- 19a Nikolai J, Schlegel J, Regitz M, Maas G. Synthesis 2002; 497
- 19b Gerster H, Espenlaub S, Maas G. Synthesis 2006; 2251
- 20 Bezenšek J, Prek B, Grošelj U, Golobič A, Stara K, Svete J, Kantlehner W, Maas G, Stanovnik B. Z. Naturforsch., B: J. Chem. Sci. 2014; 69b: 554
- 21 Kratzer P, Steinhauser S, Maas G. Z. Naturforsch., B: J. Chem. Sci. 2014; 69b: 567
- 22 Sauer J, Heldmann DK, Hetzenegger J, Krauthan J, Sichert H, Schuster J. Eur. J. Org. Chem. 1998; 2885
- 23 Usov VA, Timokhina LV, Voronkov MG. Russ. Chem. Rev. 1986; 55: 1003
- 24 Liebscher J, Hartmann H. Synthesis 1970; 241
- 25a Gupton JT, Petrich SA, Smith LL, Bruce MA, Vu P, Du KX, Dueno EE, Jones CR, Sikorski JA. Tetrahedron 1996; 52: 6879
- 25b Gompper R, Harfmann C, Polborn K. J. Prakt. Chem./Chem.-Ztg. 1998; 340: 381
- 25c Marcoux J.-F, Marcotte F.-A, Wu J, Dormer PG, Davies IW, Hughes D, Reider PJ. J. Org. Chem. 2001; 66: 4194
- 25d Davies IW, Marcoux J.-F, Kuethe JT, Lankshear MD, Taylor JD. O, Tsou N, Dormer PG, Hughes DL, Houk KN, Guner V. J. Org. Chem. 2004; 69: 1298
- 25e Clemens RT, Smith SQ. Tetrahedron Lett. 2005; 46: 1319
- 25f Gupton JT, Miller RB, Krumpe KE, Clough SC, Banner EJ, Kanters RP. F, Du KX, Keertikar KM, Lauerman NE, Solano JM, Adams BR, Callahan DW, Little BA, Scharf AB, Sikorski JA. Tetrahedron 2005; 61: 1845
- 25g Wright MT, Carroll DG, Smith TM, Smith SQ. Tetrahedron Lett. 2010; 51: 4150
- 25h Smith SQ, Dudek ST, He S.-H, Girod JA, Nunes SR. Tetrahedron Lett. 2013; 54: 3965
- 26 Balachari D, Quinn L, O’Doherty GA. Tetrahedron Lett. 1999; 40: 4769
- 27 Geyer AG, McClellan WJ, Rockway TW, Stewart KD, Weitzberg M, Wendt MD (Abbott Laboratories) US 6258822 B1, 2001 ; Chem Abstr. 2001, 502430.
- 28 Landelle H, Godard A.-M, Dadurée D, Chenu E, Robba M. Chem. Pharm. Bull. 1991; 39: 3057
- 29 Danishefsky S, Kitahara T, Yan CF, Morris J. J. Am. Chem. Soc. 1979; 101: 6996
- 30 Weingärtner W, Maas G. Eur. J. Org. Chem. 2012; 6372
- 31 Sheldrick GM. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008; 64: 112
- 32 ORTEP-3 for Windows, see: Farrugia L. J. Appl. Crystallogr. 1997; 30: 565
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