Tautomerism of α,β-Ethylenic Imines and Their Reactivity Toward Electrophilic Olefins

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1901-1904

  Jabin, Ivan ^a   Revial, Gilbert ^b   Pfau, Michel ^b   Decroix, Bernard ^a   Netchitaïlo, Pierre ^a  

^a UNIVERSITÉ DU HAVRE   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001568251     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991048o     Document Type: Article

References (25)

1. Pfau, M.; Ribière, C. J. Chem. Soc., Chem. Commun. 1970, 66-67.
2. Kametani, T.; Surgenor, S. A.; Fukumoto, K. Heterocycles 1980, 14, 303-310. Kametani, T.; Surgenor, S. A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 920-925. Kessar, S. V.; Singh, P.; Sharma, S. K. Tetrahedron Lett. 1982, 23, 4179-4180. Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397-2400. Kobor, J.; Lazar, J.; Fulop, F.; Bernath, G. J. Heterocycl. Chem. 1994, 31, 825-828. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873-4886.
3. Kametani, T.; Surgenor, S. A.; Fukumoto, K. Heterocycles 1980, 14, 303-310. Kametani, T.; Surgenor, S. A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 920-925. Kessar, S. V.; Singh, P.; Sharma, S. K. Tetrahedron Lett. 1982, 23, 4179-4180. Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397-2400. Kobor, J.; Lazar, J.; Fulop, F.; Bernath, G. J. Heterocycl. Chem. 1994, 31, 825-828. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873-4886.
4. Kametani, T.; Surgenor, S. A.; Fukumoto, K. Heterocycles 1980, 14, 303-310. Kametani, T.; Surgenor, S. A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 920-925. Kessar, S. V.; Singh, P.; Sharma, S. K. Tetrahedron Lett. 1982, 23, 4179-4180. Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397-2400. Kobor, J.; Lazar, J.; Fulop, F.; Bernath, G. J. Heterocycl. Chem. 1994, 31, 825-828. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873-4886.
5. Kametani, T.; Surgenor, S. A.; Fukumoto, K. Heterocycles 1980, 14, 303-310. Kametani, T.; Surgenor, S. A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 920-925. Kessar, S. V.; Singh, P.; Sharma, S. K. Tetrahedron Lett. 1982, 23, 4179-4180. Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397-2400. Kobor, J.; Lazar, J.; Fulop, F.; Bernath, G. J. Heterocycl. Chem. 1994, 31, 825-828. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873-4886.
6. Kametani, T.; Surgenor, S. A.; Fukumoto, K. Heterocycles 1980, 14, 303-310. Kametani, T.; Surgenor, S. A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 920-925. Kessar, S. V.; Singh, P.; Sharma, S. K. Tetrahedron Lett. 1982, 23, 4179-4180. Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397-2400. Kobor, J.; Lazar, J.; Fulop, F.; Bernath, G. J. Heterocycl. Chem. 1994, 31, 825-828. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873-4886.
7. Kametani, T.; Surgenor, S. A.; Fukumoto, K. Heterocycles 1980, 14, 303-310. Kametani, T.; Surgenor, S. A.; Fukumoto, K. J. Chem. Soc., Perkin Trans. 1 1981, 920-925. Kessar, S. V.; Singh, P.; Sharma, S. K. Tetrahedron Lett. 1982, 23, 4179-4180. Bhattacharjya, A.; Bhattacharya, P. K.; Pakrashi, S. C. Heterocycles 1983, 20, 2397-2400. Kobor, J.; Lazar, J.; Fulop, F.; Bernath, G. J. Heterocycl. Chem. 1994, 31, 825-828. Kobor, J.; Sohar, P.; Fulop, F. Tetrahedron 1994, 50, 4873-4886.
8. Hoberg, H.; Kieffer, R. Justus Liebigs Ann. Chem. 1972, 760, 141-150. Pfau, M.; Ughetto-Monfrin, J.; Joulain, D. Bull. Soc. Chim. Fr. 1979, 627-632. Tsuge, O.; Hatta, T.; Kuwata, M.; Yamashita, T.; Kakehi, A. Heterocycles 1996, 43, 2083-2090.
9. Hoberg, H.; Kieffer, R. Justus Liebigs Ann. Chem. 1972, 760, 141- 150. Pfau, M.; Ughetto-Monfrin, J.; Joulain, D. Bull. Soc. Chim. Fr. 1979, 627-632. Tsuge, O.; Hatta, T.; Kuwata, M.; Yamashita, T.; Kakehi, A. Heterocycles 1996, 43, 2083-2090.
10. Hoberg, H.; Kieffer, R. Justus Liebigs Ann. Chem. 1972, 760, 141- 150. Pfau, M.; Ughetto-Monfrin, J.; Joulain, D. Bull. Soc. Chim. Fr. 1979, 627-632. Tsuge, O.; Hatta, T.; Kuwata, M.; Yamashita, T.; Kakehi, A. Heterocycles 1996, 43, 2083-2090.
11. See ref 1. For a general reference on the chemistry of enamines, see: Rappoport, Z. The Chemistry of Enamines (The Chemistry of Functional Groups); John Wiley and son: New York, 1994.
12. Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273-274. Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references therein.
13. Pfau, M.; Revial, G.; Guingant, A.; d'Angelo, J. J. Am. Chem. Soc. 1985, 107, 273-274. Jabin, I.; Revial, G.; Melloul, K.; Pfau, M. Tetrahedron: Asymmetry 1997, 8, 1101-1109 and references therein.
14. Enones 1b,c and 3 are commercially available while enone 1a was prepared according to the literature: Warnhoff, E. W.; Martin, D. G.; Johnson, W. S. Org. Synth. Collect. Vol. IV 1967, 162-165.
15. White, W. A.; Weingarten, H. J. Org. Chem. 1967, 32, 213-214.
16. 3) δ 13.40, 21.93, 22.42, 24.66, 25.76, 54.67, 125.9, 127.1 (2C), 127.8 (2C), 130.2, 139.9, 140.8, 166.6.
17. In the case of imine 2c, only deuteration at the α′ position is possible.
18. Reaction between methyl acrylate or methyl vinyl ketone and imines 2a-c and 4 were also attempted but resulted in the degradation of the starting material. Consequently, much more reactive electrophilic olefins (i.e.. phenyl acrylate and maleic anhydride) were tested. Phenyl acrylate was prepared according to the literature: Ahlbretch, A. H.; Codding, D. W. J. Am. Chem. Soc. 1953, 75, 984.
19. This technique permits the separation of the regioisomers and the determination of their ratio. For further details, see the following reference: Jabin, I.; Revial, G.; Tomas, A.; Lemoine, P.; Pfau, M. Tetrahedron: Asymmetry 1995, 6, 1795-1812.
20. 3) δ 17.88, 25.18, 28.49, 31.49, 32.46, 38.77, 47.08, 96.60, 126.5 (2C), 126.7, 128.3 (2C), 128.5, 132.5, 137.3, 149.2, 169.1.
21. 3) δ 17.88, 25.18, 28.49, 31.49, 32.46, 38.77, 47.08, 96.60, 126.5 (2C), 126.7, 128.3 (2C), 128.5, 132.5, 137.3, 149.2, 169.1.
22. 3) δ 17.88, 25.18, 28.49, 31.49, 32.46, 38.77, 47.08, 96.60, 126.5 (2C), 126.7, 128.3 (2C), 128.5, 132.5, 137.3, 149.2, 169.1.
23. See ref 5.
24. 3OD.
25. 3) δ 18.06, 24.30, 28.50, 29.82, 43.92, 45.93, 49.10, 51.73, 88.91, 127.2 (2C), 128.5 (2C), 129.4, 131.3, 136.0, 151.7, 172.3, 174.2.