Highly regio- and stereoselective intramolecular 1,3-dipolar cycloadditions of norbornadiene-tethered nitrile oxides

Organic Letters

Volumn 1, Issue 5, 1999, Pages 791-794

  Yip, Carol ^a   Handerson, Sean ^a   Jordan, Robert ^a   Tam, William ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001090792     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990765f     Document Type: Article

References (26)

1. (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon: Oxford, 1991; Vol. 5, Chapters 1-9.
2. (b) Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, 1994; Vols. 1-3.
3. (c) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
4. (a) 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; John Wiley & Sons: New York, 1984; Vols. 1 and 2..
5. (b) Gothelf, K. V.; Jørgensen, K. A. Chem. Rev. 1998, 98, 863.
6. (a) Curran, D. P. In Advances in Cycloaddition; Curran, D. P., Ed.; JAI Press: Greenwich, 1988; Vol. 1, pp 129-189.
7. (b) Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Torssell, K. B. G., Ed.; VCH: New York, 1988.
8. (c) Kanemasa, S.; Tsuge, O. Heterocycles 1990, 30, 719.
9. Brandsma, L.; Verkuruijsse, H. D. Recl. Trav. Chim. Pays-Bas 1986, 105, 66.
10. Lautens, M.; Tam, W.; Edwards, L. G. J. Org. Chem. 1992, 57, 8.
11. Organic Functional Group Preparation; Sandler S. R., Karo, W., Eds.; Academic Press: New York, 1968; Vol. 1, pp 425-429.
12. Mukaiyama, T.; Hoshino, T. J. Am. Chem. Soc. 1960, 82, 5339.
13. Shimizu, T.; Hayashi, T.; Shibafuchi, H.; Teramura, K. Bull. Chem. Soc. Jpn. 1986, 59, 2827.
14. Basel, Y.; Hassner, A. Synthesis 1997, 309.
15. De Micheli, C.; Gandolfi, R.; Oberti, R. J. Org. Chem. 1980, 45, 1209.
16. (a) Flautt, T. J.; Erman, W. F. J. Am. Chem. Soc. 1963, 85, 3212.
17. (b) Mazzocchi, P. H.; Stahly, B.; Dodd, J.; Rondan, N. G.; Domelsmith, L. N.; Rozeboom, M. D.; Caramella, P.; Houk, K. N. J. Am. Chem. Soc. 1980, 102, 6482.
18. b. These dihedral angles were then compared to the Karplus curve for the determination of the theoretical coupling constants.
19. Lautens M.; Edwards, L. G.; Tam, W.; Lough, A. J. J. Am. Chem. Soc. 1995, 117, 10276.
20. Rosini, G.; Ballini, R.; Sorrenti, P. Synthesis 1983, 1014.
21. Heinze, I.; Knoll, K.; Mòller, R.; Eberbach, W. Chem. Ber. 1989, 122, 2147.
22. Lange, G. L.; Gottardo, C. Synth. Commun. 1990, 20, 1473.
23. We have recently developed a novel and efficient method for the preparation of unsymmetrical 2,3-disubstituted norbornadienes (e.g., compounds 29-32. These results will be reported in due course.
24. Only polymeric material was obtained. As the length ot the tether increases, the rate of intramolecular cycloaddition decreases and side reactions such as rearragement and dimerization of the nitrile oxide and polymerization could occur.
25. In all the cycloadditions, in addition to the exo-cycloadducts some dark brown polymeric materials were obtained. But in all cases, no other isomeric cycloadduct was detected by TLC and by crude NMR.
26. Recrystallization of cycloadduct 42 (R = Me) in 20% EtOAc/hexanes provided suitable crystals for X-ray analysis. Details of the X-ray analysis will be submitted for publication in Acta Crystallogr., Sect. C.