The first example of (2,5) ene cyclization: Solid acid-catalyzed oxonium-ene reaction

Journal of Organic Chemistry

Volumn 64, Issue 16, 1999, Pages 6056-6059

  Ohmura, Hirofumi ^a   Smyth, Gyles Darren ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ION; OXONIUM; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CYCLIZATION; HYDROGEN BOND; ISOMERISM; MOLECULAR DYNAMICS; MOLECULAR INTERACTION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033529960     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990682c     Document Type: Article

References (26)

1. For excellent and comprehensive reviews of intramolecular ene reactions (ene cyclizations), see: (a) Conia, J. M.; Le Perchec, P. Synthesis 1975, 1. (b) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
2. For excellent and comprehensive reviews of intramolecular ene reactions (ene cyclizations), see: (a) Conia, J. M.; Le Perchec, P. Synthesis 1975, 1. (b) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
3. For excellent and comprehensive reviews of intramolecular ene reactions (ene cyclizations), see: (a) Conia, J. M.; Le Perchec, P. Synthesis 1975, 1. (b) Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. (c) Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984.
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7. For (1,5) oxonium-ene cyclizations (Oppolzer's type III), see: (a) Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. (b) Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. (c) Blumenlopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399.
8. For (1,5) oxonium-ene cyclizations (Oppolzer's type III), see: (a) Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. (b) Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. (c) Blumenlopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399.
9. For (1,5) oxonium-ene cyclizations (Oppolzer's type III), see: (a) Overman, L. E.; Thompson, A. S. J. Am. Chem. Soc. 1988, 110, 2248. (b) Blumenkopf, T. A.; Bratz, M.; Castaneda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386. (c) Blumenlopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399.
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12. For reviews on Lewis acid promoted ene reactions, see: Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Snider, B. B. In Selectivities in Lewis Acid Promoted Reactions; Schinzer, D., Ed.; Kluwer Academic Publishers: London, 1989; pp 147-167. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vols. 2 and 5.
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17. In THF, the formation of endo product 6 was observed (3:4:5:6 = 23:63:0:13 (66% combined yield)).
18. Dimerized ether of the substrate 1 was obtained (49%).
19. The control of water content in K10 is attained as follows. First, K10 was dried completely by heating (500°C) in vacuo (0.05 Torr) for 10 h. Then, the desired amount of water was introduced.
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21. Ballantine, J. A. In Solid Supports and Catalysts in Organic Synthesis; Smith, K., Ed.; Ellis Horwood: London, 1992; Part 2, Chapter 4, pp 101-102. Laszlo, P. Preparative Chemistry Using Supported Reagents; Academic Press: New York, 1987.
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26. 2O-hexane, 1:10).