Diels-Alder Reactions of 2-(N-Acylamino)-1,3-dienes. Atypical Regioselectivity and Endo/Exo Selectivity

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3810-3811

  Ha, Jae Du ^a   Kang, Chul Hyun ^a   Belmore, Kenneth A ^a   Cha, Jin Kun ^a  

^a UNIVERSITY OF ALABAMA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000530296     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980593k     Document Type: Article

References (31)

1. (a) Overman, L. E.; Jessup, P. J. Tetrahedron Lett. 1977, 1253.
2. (b) Overman, L. E.; Clizbe, L. A. J. Am. Chem. Soc. 1976, 98, 2352 and 8295.
3. (c) Overman, L. E.; Jessup, P. J. J. Am. Chem. Soc. 1978, 100, 5179.
4. (d) Overman, L. E.; Fukaya, C. J. Am. Chem. Soc. 1980, 102, 1454.
5. (e) Jessup, P. J.; Petty, C. B.; Roos, J.; Overman, L. E. Organic Syntheses; Wiley: New York, 1988; Collect. Vol. VI, p 95.
6. (a) Oppolzer, W.; Fröstl, W. Helv. Chim. Acta 1975, 58, 590.
7. (b) Oppolzer, W.; Bieber, L.; Francotte, E. Tetrahedron Lett. 1979, 4537.
8. For example, see: (a) Hünig, S.; Kahanek, H. Chem. Ber. 1957, 90, 238. (b) Dauben, W. G.; Kozikowski, A. P. J. Am. Chem. Soc. 1974, 96, 3664. (c) Snowden, R. L. Tetrahedron Lett. 1984, 25, 3835.
9. For example, see: (a) Hünig, S.; Kahanek, H. Chem. Ber. 1957, 90, 238. (b) Dauben, W. G.; Kozikowski, A. P. J. Am. Chem. Soc. 1974, 96, 3664. (c) Snowden, R. L. Tetrahedron Lett. 1984, 25, 3835.
10. For example, see: (a) Hünig, S.; Kahanek, H. Chem. Ber. 1957, 90, 238. (b) Dauben, W. G.; Kozikowski, A. P. J. Am. Chem. Soc. 1974, 96, 3664. (c) Snowden, R. L. Tetrahedron Lett. 1984, 25, 3835.
11. For use of 1-amino-3-siloxy-1,3-dienes, see: (a) Smith, A. B., III; Wexler, B. A.; Tu, C.-Y.; Konopelski, J. P. J. Am. Chem. Soc. 1985, 107, 1308. (b) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. (c) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252 and J. Am. Chem. Soc. 1997, 119, 7165.
12. For use of 1-amino-3-siloxy-1,3-dienes, see: (a) Smith, A. B., III; Wexler, B. A.; Tu, C.-Y.; Konopelski, J. P. J. Am. Chem. Soc. 1985, 107, 1308. (b) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. (c) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252 and J. Am. Chem. Soc. 1997, 119, 7165.
13. For use of 1-amino-3-siloxy-1,3-dienes, see: (a) Smith, A. B., III; Wexler, B. A.; Tu, C.-Y.; Konopelski, J. P. J. Am. Chem. Soc. 1985, 107, 1308. (b) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. (c) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252 and J. Am. Chem. Soc. 1997, 119, 7165.
14. For use of 1-amino-3-siloxy-1,3-dienes, see: (a) Smith, A. B., III; Wexler, B. A.; Tu, C.-Y.; Konopelski, J. P. J. Am. Chem. Soc. 1985, 107, 1308. (b) Schlessinger, R. H.; Pettus, T. R. R.; Springer, J. P.; Hoogsteen, K. J. Org. Chem. 1994, 59, 3246. (c) Kozmin, S. A.; Rawal, V. H. J. Org. Chem. 1997, 62, 5252 and J. Am. Chem. Soc. 1997, 119, 7165.
15. Koikov, L. N.; Terent'ev, P. B.; Gloriozov, I. P.; Bundel', Y. G. J. Org. Chem. USSR 1984, 20, 832.
16. For reviews, see: (a) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023. (b) Krohn, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1582.
17. For reviews, see: (a) Enders, D.; Meyer, O. Liebigs Ann. 1996, 1023. (b) Krohn, K. Angew. Chem., Int. Ed. Engl. 1993, 32, 1582.
18. To our knowledge, to date only two reports have appeared on the Diels-Alder reaction of 2-(acylamino)-1,3-dienes: (a) Terada, A.; Murata, K. Bull. Chem. Soc. Jpn. 1967, 40, 1644. (b) Reference 1b; no structure was given for the cycloadduct.
19. To our knowledge, to date only two reports have appeared on the Diels-Alder reaction of 2-(acylamino)-1,3-dienes: (a) Terada, A.; Murata, K. Bull. Chem. Soc. Jpn. 1967, 40, 1644. (b) Reference 1b; no structure was given for the cycloadduct.
20. Decahydroquinoline rings are present in several major classes of alkaloids, including dendrobatid alkaloids (such as pumiliotoxin C, cis-243A, and gephrotoxin), Lycopodium alkaloids (lycodine, lycopodine, and lycodoline), luciduline, etc.
21. Ha, J. D.; Lee, D.; Cha, J. K. J. Org. Chem. 1997, 62, 4550.
22. (a) Foti, C. J.; Comins, D. J. J. Org. Chem. 1995, 60, 2656.
23. (b) Okita, T.; Isobe, M. Tetrahedron 1995, 51, 3737.
24. (c) Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257; J. Org. Chem. 1997, 62, 3592.
25. (c) Luker, T.; Hiemstra, H.; Speckamp, W. N. Tetrahedron Lett. 1996, 37, 8257; J. Org. Chem. 1997, 62, 3592.
26. 13C NMR spectra). This lack of regiocontrol is in sharp contrast with that of dienes 2b-d.
27. 1H COSY spectra of 5a, 8a, 9a,b, 11a,b, 14, 15a,b, and 16 are available in the Supporting Information.
28. For numbering, see structure 8a in Table 1.
29. Highly exo-selective Diels-Alder reactions were achieved by use of a sterically demanding dienophile: (a) Yoon, T.; Danishefsky, S. J.; de Gala, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 853. (b) Maruoka, K.; Imoto, H.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 12115.
30. Highly exo-selective Diels-Alder reactions were achieved by use of a sterically demanding dienophile: (a) Yoon, T.; Danishefsky, S. J.; de Gala, S. Angew. Chem., Int. Ed. Engl. 1994, 33, 853. (b) Maruoka, K.; Imoto, H.; Yamamoto, H. J. Am. Chem. Soc. 1994, 116, 12115.
31. Oppolzer, W. Pure Appl. Chem. 1990, 62, 1241.