Stereoselective Synthesis of Highly Functionalized 1,5-Oxa-Bridged Cyclooctenes via a 3-Oxidopyrylium-Cyclocypropene Acetal Cycloaddition

Organic Letters

Volumn 4, Issue 18, 2002, Pages 3091-3094

  Delgado, Alejandro ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

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ARTICLE;

EID: 0013217528     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0263954     Document Type: Article

References (28)

1. (a) Katrizky, A. R.; Dennis, N. Chem. Rev. 1989, 89, 827.
2. (b) Sammes, P. G.; Street, L. J. Gazz. Chim. Ital. 1986, 116, 106.
3. Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3359.
4. (a) Mascareñas, J. L. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Stamford, CT, 1999; Vol. 6, pp 1-54.
5. (b) Mascareñas, J. L.; Rumbo, A.; Castedo, L. J. Org. Chem. 1997, 62, 8620.
6. (c) Rodríguez, J. R.; Rumbo, A.; Castedo, L.; Mascareñas, J. L J. Org. Chem. 1999, 64, 966.
7. (d) Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L J. Org. Chem. 2000, 65, 2528.
8. (a) Chiu, P.; Lautens, M. In Topics in Current Chemistry; Springer-Verlag: Berlin, Germany, 1997; Vol. 190, p 1.
9. (b) Rodríguez, J. R.; Castedo, L.; Mascareñas, J. L. Synthesis 2000, 980.
10. The cycloaddition of diphenylcyclopropenone to 3-oxido-2,4,6-triphenylpyrylium ylide has been reported: Potts, K. T.; Elliot, A. J.; Sorm, M. J. Org. Chem. 1972, 37, 3838.
11. (a) Boger, D. L.; Brotherton, C. E. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 147-219.
12. (b) Tokuyama, H.; Isaka, H.; Nakamura, E. J. Am. Chem. Soc. 1992, 114, 5223.
13. 1H NMR spectra, and from NOESY and HMBC experiments.
14. Boger, D. L.; Brotherton, C. E. J. Am. Chem. Soc. 1986, 108, 6695.
15. (a) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165-198.
16. (b) Coxon, J. M.; Batiste, M. A. In The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed; J. Wiley and Sons: London, UK, 1987; Chapter 6.
17. 2O/TMSOTf seems to be an excellent way to generate highly reactive acylium cations: Zottola, M.; Venkateswara Rao, B.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1991, 969.
18. (a) Moss, R. A.; Guo, W.; Hagedorn, A.; Beveridge, R. J. Chem. Soc., Chem Commun. 1982, 19, 1102.
19. (b) Saigo, K.; Shimada, S.; Hasimoto, Y.; Hasegawa, M. Chem. Lett. 1989, 7, 1293.
20. (c) Nakamura, E.; Oshino, H.; Kuwajima, I. J. Am. Chem. Soc. 1986, 108, 3745.
21. The X-ray structure of 10 is included in the Supporting Information.
22. 2 we have detected small amounts (<10%) of a product similar to 9 but with a chloride instead of an acetate α to the enolether.
23. 2, at room temperature, leads exclusively to the acetylated derivative 8b.
24. (a) Desai, P.; Aubé, J. Org. Lett. 2000, 2, 1657.
25. (b) Andes Hess B., Jr.; Eckart, U.; Fabian, J. J. Am. Chem. Soc. 1998, 120, 12310.
26. For the calculations we used the set of programs Gaussian 98: Frisch, M. J.; Trucks, G. W.; Schelegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrewski, V. G.; Montgomery, J. J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennuci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ciolowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; González, C.; Challacombe, M.; Gill, P. M.; Johnson, B.; Chen, W.; Wong, M. W.; Andrés, J. L.; González, C.; Gordon, M. H.; Replogle, E. S.; Pople, J. A. Gaussian 98; Gaussian, Inc: Pittsburgh, PA, 1998.
27. (a) Burger, U.; Sonney, J.-M.; Vogel, P. Tetrahedron Lett. 1978, 829.
28. (b) Burger, U.; Sonney, J.-M.; Vogel, P. Helv. Chim. Acta 1980, 63, 1006.