Intramolecular Diels-Alder Reactions of Ester-Tethered 1,7,9-Decatrienoates: Bis[chloro(methyl)aluminum]trifluoromethanesulfonamide as a Catalyst

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4619-4621

  Saito, Akio ^a   Ito, Hisanaka ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

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Indexed keywords

EID: 0347811945     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026963f     Document Type: Article

References (28)

1. For reviews on IMDA reactions, see: (a) Roush, W. R. In Advances in cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 513-550. Ciganek, E. In Organic Reactions; Dauben, W. G., Ed.; John Wiley & Sons: New York, 1984; Vol. 32, pp 1-374. Weinreb, S. W. Acc. Chem. Res. 1985, 18, 16.
2. For reviews on IMDA reactions, see: (a) Roush, W. R. In Advances in cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 513-550. Ciganek, E. In Organic Reactions; Dauben, W. G., Ed.; John Wiley & Sons: New York, 1984; Vol. 32, pp 1-374. Weinreb, S. W. Acc. Chem. Res. 1985, 18, 16.
3. For reviews on IMDA reactions, see: (a) Roush, W. R. In Advances in cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 513-550. (c) Ciganek, E. In Organic Reactions; Dauben, W. G., Ed.; John Wiley & Sons: New York, 1984; Vol. 32, pp 1-374. Weinreb, S. W. Acc. Chem. Res. 1985, 18, 16.
4. For reviews on IMDA reactions, see: (a) Roush, W. R. In Advances in cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, CT, 1990; Vol. 2, pp 91-146. (b) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, UK, 1991; Vol. 5, pp 513-550. Ciganek, E. In Organic Reactions; Dauben, W. G., Ed.; John Wiley & Sons: New York, 1984; Vol. 32, pp 1-374. (d) Weinreb, S. W. Acc. Chem. Res. 1985, 18, 16.
5. For references of natural product syntheses, see: (a) Fallis, A. G. Acc. Chem. Rev. 1999, 32, 464-474. (b) Suzuki, Y.; Murata, T.; Takao, K.; Tadano, K. J. Synth. Org. Chem. 2002, 60, 679-689.
6. For references of natural product syntheses, see: (a) Fallis, A. G. Acc. Chem. Rev. 1999, 32, 464-474. (b) Suzuki, Y.; Murata, T.; Takao, K.; Tadano, K. J. Synth. Org. Chem. 2002, 60, 679-689.
7. (a) Boeckman, R. K., Jr.; Demko, D. M. J. Org. Chem. 1982, 47, 1789-1792.
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9. (a) Nakanishi, H.; Fujita, H.; Yamamoto, O. Bull. Chem. Soc. Jpn. 1978, 51, 214.
10. (b) Parker, K. A.; Adamchuk, M. R. Tetrahedron Lett. 1978, 1689-1692.
11. (c) Perrin, C. L.; Young, D. B. Tetrahedron Lett. 1995, 36, 7185-7188.
12. (d) Toyota, M.; Wada, Y.; Fukumoto, K. Heterocycles 1993, 35, 111-114.
13. Polar solvent effect on the IMDA reaction of ester-tethered substrates: (a) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469-5470. (b) Jung, M. E. Synlett 1990, 4, 186-190. See also intramolecular radical addition of allyl α-iodoalkanoates in water: Yoshimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omote, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041-11047.
14. Polar solvent effect on the IMDA reaction of ester-tethered substrates: (a) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469-5470. (b) Jung, M. E. Synlett 1990, 4, 186-190. See also intramolecular radical addition of allyl α-iodoalkanoates in water: Yoshimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omote, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041-11047.
15. Polar solvent effect on the IMDA reaction of ester-tethered substrates: (a) Jung, M. E.; Gervay, J. J. Am. Chem. Soc. 1989, 111, 5469-5470. (b) Jung, M. E. Synlett 1990, 4, 186-190. See also intramolecular radical addition of allyl α-iodoalkanoates in water: Yoshimitsu, H.; Nakamura, T.; Shinokubo, H.; Oshima, K.; Omote, K.; Fujimoto, H. J. Am. Chem. Soc. 2000, 122, 11041-11047.
16. Efficient IMDA reactions employing hydroxamate tethers have been reported. Ichikawa, T.; Senzaki, M.; Kadoya, R.; Morimoto, T.; Miyake, N.; Izawa, M.; Saito, S.; Kobayashi, H. J. Am. Chem. Soc. 2001, 123, 4607-4608.
17. (a) Jung, M. E.; Huang, A.; Johnson, T. W. Org. Lett. 2000, 2, 1835-1837.
18. For theoretical discussions of the transition states in the IMDA reaction of 1,3,9-decatrienoates, see: (b) Tantillo, D. J.; Houk, K. N.; Jung, M. E. J. Org. Chem. 2001, 66, 1938-1940. See also ref 4a.
19. For theoretical discussions of the transition states in the IMDA reaction of 1,3,9-decatrienoates, see: (b) Tantillo, D. J.; Houk, K. N.; Jung, M. E. J. Org. Chem. 2001, 66, 1938-1940. (c) See also ref 4a.
20. (a) Boeckman, R. K., Jr.; Flam, C. J. Tetrahedron Lett. 1983, 24, 5035-5038.
21. (b) Alexakis, A.; Jachiet, D.; Toupet, L. Tetrahedron 1989, 45, 6203-6210.
22. (10) For examples of significant activation of the carbonyl group by a bidentate Lewis acid, see: (a) Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5365-5368. (b) Hanawa, H.; Maekawa, N.; Maruoka, K. Tetrahedron Lett. 1999, 40, 8379-8382.
23. For examples of significant activation of the carbonyl group by a bidentate Lewis acid, see: (a) Hanawa, H.; Maruoka, K. Tetrahedron Lett. 1999, 40, 5365-5368. (b) Hanawa, H.; Maekawa, N.; Maruoka, K. Tetrahedron Lett. 1999, 40, 8379-8382.
24. Kim, P.; Hantz, M. H.; Kurth, M. J.; Olmstead, M. M. Org. Lett. 2000, 2, 1831-1834.
25. 2. It has been reported that bis(trimethylsilyl)trifluoromethanesulfonamide exists as a mixture of N,N- and N,O-bis-silylated forms in solution, see: Jonas, S.; Westerhausen, M.; Simchen, G. J. Organomet. Chem. 1997, 548, 131-137.
26. Thermal IMDA reaction of 2c (210°C, 5 h) was reported to give the cycloadduct (42% yield) as a mixture of stereoisomers. See ref 4b.
27. To the best of our knowledge, no successful example of the IMDA reaction of 1,3,9-decatriene systems tethered by an α-substituted ester moiety such as a methacrylate 2g has been reported.
28. 2 complex at room temperature showed broadened signals indicating the existence of plural complex forms in relatively slow equilibrium, which, at -50°C, turned to sharp signals of a mixture of three sets of complexes in a ratio of 3:2:1.