Intermolecular 1,3-dipolar cycloadditions of azomethine imines

Arkivoc

Volumn 2007, Issue 5, 2007, Pages 152-166

  Jones, Raymond C F ^a   Hollis, Stephen J ^b   Iley, James N ^b  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b OPEN UNIVERSITY   (United Kingdom)

Author keywords

1,3 dipole; Azomethine imine; Pyrazolidine

Indexed keywords

EID: 33846121008     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.513     Document Type: Article

References (23)

1. (a) Jones, R. C. F.; Hollis S. J.; Iley, J. N. Tetrahedron: Asymmetry, 2000, 11, 3273.
2. (b) Jones, R. C. F.; Gilbert, I. H.; Rees D. C.; Crockett, A. K. Tetrahedron 1995, 51, 6315.
3. cf.: Dutta, A. S.; Morley, J. S. J. Chem. Soc., Perkin Trans. 1 1975, 1712.
4. Mish, M. R.; Guerra, F. M.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 8379.
5. See, for example: Advances in Amino Acid Mimetics and Peptidomimetics, Abell, A., Ed.; Jai Press Inc, Stamford (USA), 1999; Vol. 2.
6. Grashey, R. in 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley: New York, 1984, p. 733.
7. See, for example: Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996 52, 901.
8. Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Am. Chem. Soc. 1984, 106, 5594.
9. Oppolzer, W. Tetrahedron Lett. 1970, 3091.
10. Oppolzer, W. Tetrahedron Lett. 1970, 2199.
11. Huisgen, R.; Grashey, R.; Sauer, J. The Chemistry of Alkenes, Patai, S., Ed.; Wiley-Interscience, New York, 1964; p. 849 et seq.
12. Roussi, F.; Chauveau, A.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2000, 1170.
13. Chauveau, A.; Martens, T.; Bonin, M.; Micouin, L.; Husson, H.-P. Synthesis 2002, 1885.
14. Condon, F. E. J. Org. Chem. 1972, 37, 3608.
15. Experiments carried out in an NMR tube with d8-toluene showed that heating for 72 h was required for complete reaction of the dipole to occur.
16. Dorn, H. Tetrahedron Lett. 1985, 26, 5123.
17. Kanemasa, S.; Tomoshige, N.; Wada, E.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 3944.
18. In all cycloadditions carried out with mono-substituted dipolarophiles, where two 4-substituted pyrazolidines were observed, the isomer identified as syn- was less polar in TLC analysis on silica than the anti- isomer. The chemical shift of the methine proton at C-4 was also found to be greater for the syn-isomer than for the anti-isomer (δ; 3.94 ppm for 10 and δ 3.45 for 11). Values for this proton in 21 and 22 are δ 3.76 and δ 3.05, respectively.
19. Chung, Y. J.; Ryu, E. J.; Keum, G.; Kim, B. H. Bioorg. Med. Chem. 1996, 4, 209.
20. Reetz, M. T.; Drewes, M. W.; Schmitz, A. Angew. Chem., Int. Ed. Engl. 1987, 26, 1141.
21. Calabretta, R.; Gallina, C.; Giordano, C. Synthesis 1991, 536.
22. Lenman, M. M.; Lewis, A.; Gani, D. J. Chem. Soc., Perkin Trans. 1 1997, 2297.
23. rd Edn.; Pergamon Press: Oxford, 1988.