Unusual Regioselectivity of the Dipolar Cycloaddition Reactions of Nitrile Oxides and Tertiary Cinnamides and Crotonamides

Journal of Organic Chemistry

Volumn 63, Issue 18, 1998, Pages 6319-6328

  Weidner Wells, Michele A ^a   Fraga Spano, Stephanie A ^a   Turchi, Ignatius J ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001374653     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9807621     Document Type: Article

References (37)

1. This work was presented in part at the ACS National Meeting in Chicago, IL, in August 1995.
2. Department of Process Chemistry.
3. (a) Quilico, A. In Five and Six Membered Compounds with Nitrogen and Oxygen; Wiley, R. H., Ed.; Interscience Publishers: New York, 1962.
4. (b) Torssell, K. Nitrile Oxides, Nitrones and Nitronates in Organic Synthesis; VCH: New York, 1988.
5. Caramella, P.; Grünanger, P. In 1,3-Dipolar Cycloaddition Chemistry, Vol. 1; Padwa, A., Ed.; Wiley: New York, 1984.
6. Grünanger, P.; Vita-Finzi, P. Isoxazoles-Part 1; Vol. 49 of Chemistry of Heterocyclic Compounds; Wiley: New York, 1991 and references cited therein.
7. (a) Huisgen, R.; Christl, M. Chem. Ber. 1973, 106, 3275.
8. (b) Huisgen, R.; Christl, M. Chem. Ber. 1973, 106, 3345.
9. Monforte, F. Gazz. Chim. Ital. 1952, 82, 130.
10. DeSarlo, F.; Guarna, A.; Brandi, A. J. Heterocycl. Chem. 1983, 20, 1505.
11. Weidner-Wells, M. A.; Fraga, S. A.; Demers, J. P. Tetrahedron Lett. 1994, 35, 6473.
12. Liu, K.; Shelton, B.; Howe, R. K. J. Org. Chem. 1980, 45, 3916.
13. Sustmann, R.; Huisgen, R.; Huber, H. Chem. Ber. 1967, 100, 1802.
14. Curran, D. P.; Choi, S.-M.; Gothe, S. A.; Lin, F.-T. J. Org. Chem. 1990, 55, 3710.
15. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley: New York, 1976.
16. Kamimura, A.; Hori, K. Tetrahedron 1994, 50, 7969.
17. Dewar, M. J. S.; Zoenison, E. G.; Healy, E. F. J. Am. Chem. Soc. 1985, 107, 3902.
18. Brown, F. K.; Singh, U. C.; Kollman P. A.; Raimondi, L.; Houk, K. N.; Bock, C. W. J. Org. Chem. 1992, 57, 4862.
19. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
20. ‡ for the 4- and 5-regioisomers are <2 eu.
21. RHF/6-31G(dV//RHF/3-21G single-point calculated energies give only slightly better results than the RHF/3-21G calculations with the 4-regioisomer predominating in each case while MP2/6-31G(d)//RHF/ 3-21G single-point calculations predict that the 5-regioisomers predominate in each case.
22. (a) Yoo, H. Y.; Houk, K. N. J. Am. Chem. Soc. 1997, 119, 2877.
23. (b) Wiest, O. Houk, K. N. Top. Gurr. Chem. 1996, 183 (Density Functional Theory IV), 1.
24. Delaney, A. D.; Currie, D. J.; Holmes, H. L. Can. J. Chem. 1969, 47, 3273.
25. Fahmy, A. F.; Sayed, G. H.; Hamed, A. A. Ind. J. Chem. Soc. B 1978, 16B, 869.
26. Yamaguchi, K. Nippon Kagaku Zasshi 1957, 78, 1236; Chem. Abstr. 1958, 13540.
27. Yamaguchi, K. Nippon Kagaku Zasshi 1957, 78, 1236; Chem. Abstr. 1958, 13540.
28. Coates, R. M.; Johnson, E. F. J. Am. Chem. Soc. 1971, 93, 401b.
29. Currie, D. J.; Holmes, H. L. Can. J. Chem. 1970, 48, 1340.
30. Chan, S.O.; Welis, E. J. Can. J. Chem. 1967, 45, 2123.
31. Tung, C. C.; Speziale, A. J. J. Org. Chem. 1964, 29, 1577.
32. Mitsudo, T.; Suzuki, N.; Kondo, T.; Watanabe, Y. J. Org. Chem. 1994, 59, 7759.
33. Maier, L. Helv. Chim. Acta 1973, 56, 1252.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Gill, P. M. W.; Johnson, B. G.; Robb, M. A.; Cheeseman, J. R.; Keith, T.; Petersson, G. Al-Laham, M. A.; Zakrzewski, V. G.; Ortiz, J. V.; Foresman, J. B.; Cioslowski, J.; Stefanov, B. B.; Nanayakkara, A.; Challacombe, M.; Peng, C. Y; Ayala, P. Y.; Chen, W.; Wong, M. W.; Andres, J. L.; Replogle, E. S.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Binkley, J. S.; Defrees, D. J.; Baker, J.; Stewart, J. P.; Head-Gordon, M.; Gonzalez, C.; Pople, J. A. Gaussian 94, Revision E.1; Gaussian, Inc.: Pittsburgh, PA, 1995.
35. SPARTAN (v. 4.1), Wavefunction, Inc., Irvine, CA.
36. CAChe Scientific, Oxford Molecular, Beaverton, OR.
37. Becke, A. D. J. Chem. Phys. 1993, 98, 5648.