Diels-Alder reactions of 5-vinyl-1-acyl-2-aryl-2,3-dihydro-4-pyridones: Regio- and stereoselective synthesis of octahydroquinolines

Organic Letters

Volumn 5, Issue 3, 2003, Pages 321-323

  Kuethe, Jeffrey T ^a   Brooks, Clinton A ^a   Comins, Daniel L ^a  

^a NORTH CAROLINA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 PYRIDONE DERIVATIVE; QUINOLINE DERIVATIVE; PYRIDONE DERIVATIVE;

ARTICLE; CYCLIZATION; DIELS ALDER REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

MOLECULAR STRUCTURE; PYRIDONES; QUINOLINES; STEREOISOMERISM;

EID: 0038751918     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol027308a     Document Type: Article

References (26)

1. For leading references, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Nicolau, K. C.; Snyder, S. A.; Montagnon, T.; Vassiligiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668. (c) Tietze, L. F.; Kettschau, G. In Topics in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 189, pp 1-120 and references therein. (d) Waldmann, H. Synthesis 1994, 535.
2. For leading references, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Nicolau, K. C.; Snyder, S. A.; Montagnon, T.; Vassiligiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668. (c) Tietze, L. F.; Kettschau, G. In Topics in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 189, pp 1-120 and references therein. (d) Waldmann, H. Synthesis 1994, 535.
3. For leading references, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Nicolau, K. C.; Snyder, S. A.; Montagnon, T.; Vassiligiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668. (c) Tietze, L. F.; Kettschau, G. In Topics in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 189, pp 1-120 and references therein. (d) Waldmann, H. Synthesis 1994, 535.
4. For leading references, see: (a) Corey, E. J. Angew. Chem., Int. Ed. 2002, 41, 1650. (b) Nicolau, K. C.; Snyder, S. A.; Montagnon, T.; Vassiligiannakis, G. Angew. Chem., Int. Ed. 2002, 41, 1668. (c) Tietze, L. F.; Kettschau, G. In Topics in Current Chemistry; Metz, P., Ed.; Springer-Verlag: Berlin, 1997; Vol. 189, pp 1-120 and references therein. (d) Waldmann, H. Synthesis 1994, 535.
5. For reviews on the Diels-Alder reaction of amino-substituted dienes, see: (a) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023. (b) Barluenga, J.; Suarez-Sobrino, A.; Lopez, L. A. Aldrichim. Acta 1997, 32, 4.
6. For reviews on the Diels-Alder reaction of amino-substituted dienes, see: (a) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023. (b) Barluenga, J.; Suarez-Sobrino, A.; Lopez, L. A. Aldrichim. Acta 1997, 32, 4.
7. (a) Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352.
8. (b) Overman, L. E.; Taylor, G. F.; Jessup, P. J. Tetrahedron Lett. 1976, 3089.
9. (c) Overman, L. E.; Yaylor, G. F.; Houk, K. N.; Domelsmith, L. S. J. Am. Chem. Soc. 1978, 100, 3182.
10. (d) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537.
11. (e) Overman, L. E.; Freerks, R. L.; Petty, C. B.; Clizbe, L. A.; Ono, R. K.; Taylor, G. F.; Jessup, P. J. J. Am. Chem. Soc. 1981, 103, 2816.
12. (a) Ha, J. D.; Kang, C. H.; Belmore, K. A.; Cha, J. K. J. Org. Chem. 1998, 63, 3810 and references therein.
13. (b) Aelterman, W.; De Kimpe, N. Tetrahedron 1998, 54, 2563.
14. (c) Brosius, A. D.; Overman, L. E.; Schwink, L. J. Am. Chem. Soc. 1999, 121, 700.
15. (d) Jiang, J.; DeVita, R. J.; Doss, G. A.; Goulet, M. T.; Wyvratt, M. J. J. Am. Chem. Soc. 1999, 121, 593.
16. (e) Barluenga, J.; Fernandez, M. A.; Aznar, F.; Valdes, C. Tetrahedron Lett. 2002, 43, 8159 and references therein.
17. For leading references, see: (a) Comins, D. L.; Al-awar, R. S.; Foti, C. J. J. Org. Chem. 1999, 64, 2184. (b) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (c) Comins, D. L.; Fulp, A. B. Org. Lett. 1999, 1, 1941. (d) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855. (e) Huang, S.; Comins, D. L. Chem. Commun. 2000, 7, 569.
18. For leading references, see: (a) Comins, D. L.; Al-awar, R. S.; Foti, C. J. J. Org. Chem. 1999, 64, 2184. (b) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (c) Comins, D. L.; Fulp, A. B. Org. Lett. 1999, 1, 1941. (d) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855. (e) Huang, S.; Comins, D. L. Chem. Commun. 2000, 7, 569.
19. For leading references, see: (a) Comins, D. L.; Al-awar, R. S.; Foti, C. J. J. Org. Chem. 1999, 64, 2184. (b) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (c) Comins, D. L.; Fulp, A. B. Org. Lett. 1999, 1, 1941. (d) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855. (e) Huang, S.; Comins, D. L. Chem. Commun. 2000, 7, 569.
20. For leading references, see: (a) Comins, D. L.; Al-awar, R. S.; Foti, C. J. J. Org. Chem. 1999, 64, 2184. (b) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (c) Comins, D. L.; Fulp, A. B. Org. Lett. 1999, 1, 1941. (d) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855. (e) Huang, S.; Comins, D. L. Chem. Commun. 2000, 7, 569.
21. For leading references, see: (a) Comins, D. L.; Al-awar, R. S.; Foti, C. J. J. Org. Chem. 1999, 64, 2184. (b) Comins, D. L.; Brooks, C. A.; Al-awar, R. S.; Goehring, R. R. Org. Lett. 1999, 1, 229. (c) Comins, D. L.; Fulp, A. B. Org. Lett. 1999, 1, 1941. (d) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855. (e) Huang, S.; Comins, D. L. Chem. Commun. 2000, 7, 569.
22. Comins, D. L.; Joseph, S. P.; Chen, X. Tetrahedron Lett. 1995, 36, 9141.
23. Details can be found in Supporting Information.
24. Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles; Moody, C. J., Ed.; JAI Press: Greenwich, CT, 1996; Vol. 2, pp 251-294 and references therein.
25. (a) Comins, D. L.; Joseph, S. P.; Goehring, R. R. J. Am. Chem. Soc. 1994, 116, 4719.
26. (c) Comins, D. L.; Guerra-Weltzien, L. Tetrahedron Lett. 1996, 37, 3807.