The preparation of rigid alicyclic molecules bearing effector groups from alkene blocks using s-tetrazines and 1,3,4-triazines as stereoselective coupling agents

Synlett

Volumn , Issue 6, 1998, Pages 585-587

  Warrener, Ronald N ^a   Margetic, Davor ^a   Russell, Richard A ^b  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b DEAKIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001368899     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1735     Document Type: Article

References (19)

1. Building BLOCKs in Synthesis Part 3,
2. for part 2, see Warrener, R. N.; Butler, D. N.; Russell, R. A. Synlett 1998, 566.
3. Warrener, R. N.; Schultz, A. C.; Butler, D. N.; Wang, S.; Mahadevan, I. B.; Russell, R. A. Chem. Commun. 1997, 1023.
4. Butler, D. N.; Malpass, J. R.; Margetic, D.; Russell, R. A.; Sun, G.; Warrener, R. N. Synlett 1998, 588.
5. Boger, D. L.; Weinreb, S. N. "Hetero Diels-Alder Methodology in Organic Synthesis" Academic Press, San Diego, 1987.
6. 6 where it was established that norbornene 1 reacted with dimethyl s-tetrazine-3,6-dicarboxylate 2a to form the coupled product 4a. However, the reaction was not general and other s-tetrazines, eg 2b, could not be employed owing to a competitive rearrangement of the initially formed 4,5-dihydro pyridazine 4b to the isomeric 1,4-dihydro pyridazine 5b.
7. Dittmar, W.; Heinrichs, G.; Steigel, A.; Troll, T.; Sauer, J. Tetrahedron Lett. 1970, 1623.
8. Use of thermal conditions, even in the presence of triethylamine causes formation of much 5b in competition with the bimolecular reaction to yield 4b.
9. Warrener, R. N.; Elsey, G. M.; Sankar, I. V.; Butler, D. N.; Pekos, P.; Kennard, C. H. L. Tetrahedron Lett. 1994, 35, 6745.
10. All new products gave satisfactory spectroscopic and analytical data (accurate mass or combustion).
11. Warrener, R. N.; Butler, D. N.; Liao, W.-Y.; Pitt, I. G.; Russell, R. A. Tetrahedron Lett. 1991, 32, 1889.
12. Warrener, R. N.; Ferreira, A. B. B.; Tiekink, E. R. T. Tetrahedron Lett. 1996, 37, 2161.
13. SPARTAN v 4.1.1, Wavefunction, Inc., California, 1996.
14. 18
15. Dittmar, W.; Sauer, J.; Steigel, A. Tetrahedron Lett. 1969, 5171.
16. Elix, J. A.; Wilson, W. S.; Warrener, R. N. Tetrahedron Lett. 1970, 1837.
17. Elix, J. A.; Wilson, W. S.; Warrener, R. N.; Calder, I. C. Aust. J. Chem. 1972, 25, 865.
18. Barlow, M. G.; Haszeldine, R. N.; Simpkin, D. J. J. Chem. Soc., Perkin 1 1982, 1245.
19. Boger, D. L.; Panek, J. S. J. Am. Chem. Soc. 1985, 107, 5745.