A 1,3-dipolar cycloaddition route to 7-azanorbornanes: Application to the synthesis of syn-facial N-bridged polynorbornanes

Synlett

Volumn , Issue 6, 1998, Pages 588-589

  Butler, Douglas N ^a   Malpass, John R ^a,b   Margetic, Davor ^a   Russell, Richard A ^a,c   Sun, Guangxing ^a   Warrener, Ronald N ^a  

^a CENTRAL QUEENSLAND UNIVERSITY   (Australia)

^b UNIVERSITY OF LEICESTER   (United Kingdom)

^c DEAKIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003086676     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-3134     Document Type: Article

References (15)

1. Building BLOCKs in Synthesis Part 4,
2. for part 3, see Warrener, R. N.; Margetic, D.; Russell, R. A. Synlett 1998, 585.
3. inter alia Jones, C. D.; Simpkins, N. S. Tetrahedron Lett. 1998, 39, 1021, 1023 and references therein.
4. Sasaki, T.; Manabe, T.; Nishida, S. J. Org. Chem. 1980, 45, 476 and 479.
5. Warrener, R. N.; Schultz, A. C.; Butler, D. N.; Wang, S.; Mahadevan, I. B.; Russell, R. A. Chem. Commun. 1997, 1023.
6. For an earlier report on the preparation of polarofacial molecules based on 7-oxanorbornanes, see Warrener, R. N.; Butler, D. N.; Liao, W. Y.; Pitt, I. G.; Russell, R. A. Tetrahedron Lett. 1991, 32, 1889.
7. Meinwald, J.; Wiley, G. A. J. Am. Chem. Soc. 1958, 80, 3667.
8. Mitsudo, T.; Naruse, H.; Kondo, T.; Ozaki, Y.; Watanabe, Y. Angew. Chem., Int. Ed. 1994, 33, 580.
9. Mitsudo, T.; Kokuryo, K.; Shinsugi, T.; Nakagawa, Y.; Watanabe, Y.; Takegami, Y. J. Org. Chem. 1979, 44, 4492.
10. 3) δ 1.40 (4H, s), 1.94 (2H, s), 2.23 (4H, s), 2.71 (2H, s). 3.69 (12H, s), 3.78 (4H, s), 4.94 (4H, dbr), 5.17 (4H, s), 7.10-7.26 (28H, m).
11. 12
12. R. Huisgen, "1,3-Dipolar Cycloaddition Chemistry", Ed A. Padwa, Wiley-Interscience, 1984.
13. inter alia Davies, J. W.; Durrant, M. L.; Walker, M. P.; Belkacemi, B.; Malpass, J. R. Tetrahedron 1992, 48, 861.
14. Malpass, J. R.; Warrener, R. N.; Margetic, D.; Sun, G.; Butler, D. N., 1997, unpublished results.
15. Azides have been reported to react with alkenes under high pressure. Anderson, G. T.; Henry, J. R.; Weinreb, S. M. J. Org. Chem. 1991, 56, 6946.