Nucleophilic reaction of 1,8-diazabicyclo[5.4.0]undec-7-ene and 1,5-diazabicyclo[4.3.0]non-5-ene with methyl pheophorbide a. Unexpected products

Tetrahedron

Volumn 52, Issue 3, 1996, Pages 849-860

  Ma, Lifu ^a   Dolphin, David ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PORPHYRIN DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030025268     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00944-2     Document Type: Article

References (20)

1. For excellent reviews of trialkylsilyl triflates, see: (a). Emde, H.; et al. Synthesis 1982, 1-26.
2. (b). Noyori, R.; Murata, S.; Suzuki, M. Tetrahedron 1981, 3899-3910.
3. (a). Brownbridge, P. Synthesis 1983, 1-28; 85-104;
4. (b). Aizpurua, J. M.; Palomo, C. Tetrahedron Lett. 1985, 26(4), 475-476;
5. (c). Kim, S.; Chang, H. Bull. Chem. Soc. Jpn. 1985, 58, 3669-3670.
6. For a review of DBU and DBN, see: Oediger, H.; Moller, F.; Eiter, K. Synthesis 1972, 591-598.
7. Murata, S.; Suzuki, M.; Noyori, R. Tetrahedron 1988, 44(13), 4259-4275.
8. Sheldon, J. C.; Hayes, R. N.; Bowie, J. H. J. Am. Chem. Soc. 1984, 106, 7711-7715.
9. Wasielewski, M. R.; Thompson, J. F. Tetrahedron Lett. 1978, 1043-1046.
10. Hynninen, P. H.; Wasielewski, M. P.; Katz, J. J. Acta Chem. Scand. B 1979, 33, 637-648.
11. Ma, L.; Dolphin, D. Tetrahedron: Asymmetry, 1995, 6(2), 313-316.
12. Pennington, P. C.; Boyd, S. D.; Horton, H.; Taylor, S. W.; Wulf, D. G.; Katz, J. J.; Strain, H. H. J. Am. Chem. Soc. 1967, 89(15), 3871-3875.
13. Hynninen, P. H. J. Chromatogr. 1979, 175, 89-95.
14. Reed, R.; Reau, R.; Dahan, F.; Bertrand, G. Angew. chem. Int. Ed. Engl. 1993, 32, 399-401.
15. Lammers, H.; Cohen-Fernandes, P.; Habraken, C. L. Tetrahedron 1994, 50(3), 865-870.
16. C 21.75; 25.23; 27.74; 28.93; 36.53; 43.45; 47.51; 51.94; 160.33 ppm.
17. Fuhrhop, J. H.; Smith, K. M. Laboratory Methods in Porphyrin and Metalloporphyrin Research, Elsevier Scientific Publishing Company: Amsterdam. 1975; pp. 132-133.
18. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon Press: Oxford. 1983; pp. 101-162.
19. Smith, K. M.; Goff, D. A.; Simpson, D. J. J. Am. Chem. Soc. 1985, 107, 4946-4954.
20. Fischer, H.; Orth, H. Die Chemie Des Pyrrols, Johnson Reprint Corporation: New York. 1968; Vol. II, Part 2, pp. 64-66.