Cycloaddition reactions of aldimines of 1,5-ketoaldehydes. Applications in the synthesis of polycyclic nitrogen heterocycles

Tetrahedron

Volumn 55, Issue 6, 1999, Pages 1763-1780

  Grigg, Ronald ^a   Thornton Pett, Mark ^a   Yoganathan, Gnanamoly ^a  

^a UNIVERSITY OF LEEDS   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC 1,5 KETOALDEHYDE; ALDIMINE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; MOLECULAR MODEL; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0033524712     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01189-2     Document Type: Article

References (24)

1. Grigg, R.; Sridharan, V., Advances in Cycloaddition, Ed. D.P. Curran, JAI Press, 1993, Vol.3, p. 161-204.
2. Grigg, R.; Hargreaves, S.; Redpath, J.; Turchi, S.; Yoganathan, G., Synthesis. In press.
3. Daly, J.W.; Witkop, B.; Tokuyama, T.; Nishikawa, T.; Karle. I.L., Helv. Chem. Acta., 1977, 60, 1128-1140.
4. Ranu, B.C.; Bhar, S.; Sarkar, D.C., Tetrahedron Lett., 1991, 32, 2811-2812. Ranu, B.C.; Bhar, S., Tetrahedron, 1992, 48, 1327-1332. Cope, C.; Synerholm, M.E., J. Am. Chem. Soc., 1950, 72, 5228-5232. Baker, B.R.; Shapiro, H.S., J. Med. Chem., 1963, 6, 664-669.
5. Ranu, B.C.; Bhar, S.; Sarkar, D.C., Tetrahedron Lett., 1991, 32, 2811-2812. Ranu, B.C.; Bhar, S., Tetrahedron, 1992, 48, 1327-1332. Cope, C.; Synerholm, M.E., J. Am. Chem. Soc., 1950, 72, 5228-5232. Baker, B.R.; Shapiro, H.S., J. Med. Chem., 1963, 6, 664-669.
6. Ranu, B.C.; Bhar, S.; Sarkar, D.C., Tetrahedron Lett., 1991, 32, 2811-2812. Ranu, B.C.; Bhar, S., Tetrahedron, 1992, 48, 1327-1332. Cope, C.; Synerholm, M.E., J. Am. Chem. Soc., 1950, 72, 5228-5232. Baker, B.R.; Shapiro, H.S., J. Med. Chem., 1963, 6, 664-669.
7. Ranu, B.C.; Bhar, S.; Sarkar, D.C., Tetrahedron Lett., 1991, 32, 2811-2812. Ranu, B.C.; Bhar, S., Tetrahedron, 1992, 48, 1327-1332. Cope, C.; Synerholm, M.E., J. Am. Chem. Soc., 1950, 72, 5228-5232. Baker, B.R.; Shapiro, H.S., J. Med. Chem., 1963, 6, 664-669.
8. Audisio, G.; Porzio, W.; Zetta, J.; Ferruti, P., J. Chem. Soc., Perkin Trans. 11, 1979, 1391-1394.
9. Grigg, R.; Montgomery, J.; Somasunderam, A., Tetrahedron, 1992, 48, 10431-10442.
10. Borch, R.F.; Bernstein, M.D.; Durst, H.D., J. Am. Chem. Soc., 1971, 93, 2897-2904. Lane, C.F., Synthesis, 1975, 135-146.
11. Borch, R.F.; Bernstein, M.D.; Durst, H.D., J. Am. Chem. Soc., 1971, 93, 2897-2904. Lane, C.F., Synthesis, 1975, 135-146.
12. Manescalchi, F.; Nardi, A.R.; Savoia, D., Tetrahedron Lett., 1994, 35, 2775-2778. Mattson, R.J.; Pham, K.M.; Leuck, D.J.; Cowen, K.A., J. Org. Chem., 1990, 55, 2552-2554.
13. Manescalchi, F.; Nardi, A.R.; Savoia, D., Tetrahedron Lett., 1994, 35, 2775-2778. Mattson, R.J.; Pham, K.M.; Leuck, D.J.; Cowen, K.A., J. Org. Chem., 1990, 55, 2552-2554.
14. Ihara, M.; Taniguchi, T.; Makita, K.; Takano, M.; Ohnishi, M.; Taniguchi, N.; Fukumoto, K.; Kabuto, C., J. Am. Chem. Soc., 1993, 115, 8107-8115.
15. Rejek, M.; Wimmer, Z.; Saman, D.; Ricankova, M.; Nemec, V., Helv. Chem. Acta., 1994, 77, 1241-1255.
16. Hayakawa, K.; Takewaki, M.; Fujimoto, I.; Kanematsu, K., J. Org. Chem., 1986, 57, 5100-5105.
17. Vebrel, J.; Carrie, R., Bull. Soc. Chim. Fr., 1982, 161-166. Ghosh, A.K.; Liu, W., J. Org. Chem., 1995, 60, 6198-6201. Corey, E.J.; Pine, S.G., Tetrahedron Lett., 1983, 2821-2824.
18. Vebrel, J.; Carrie, R., Bull. Soc. Chim. Fr., 1982, 161-166. Ghosh, A.K.; Liu, W., J. Org. Chem., 1995, 60, 6198-6201. Corey, E.J.; Pine, S.G., Tetrahedron Lett., 1983, 2821-2824.
19. Vebrel, J.; Carrie, R., Bull. Soc. Chim. Fr., 1982, 161-166. Ghosh, A.K.; Liu, W., J. Org. Chem., 1995, 60, 6198-6201. Corey, E.J.; Pine, S.G., Tetrahedron Lett., 1983, 2821-2824.
20. Savic, V., Ph. D. Thesis, University of Leeds, 1994, p.71.
21. Barr, D.A.; Dorrity, M.J.; Grigg, R.; Hargreaves, S.; Malone, J.F.; Montgomery, J.; Redpath, J.; Stevenson, P.; Thornton-Pett, M., Tetrahedron, 1995, 51, 273-294.
22. Gordon, A.J.; Ford, R.A., The Chemist's Companion, John Wiley & Sons, 1972, p.431 and p.434.
23. Sheldrick, G.M., Acta. Crystallogr., Sect A, 1990, 46, 467.
24. Sheldrick, G.M., SHELXL-97, Program for Refinement of Crystal Structures, University of Gottingen.