Cycloadditions of nitrile oxides to the highly reactive N-acyl-2-oxa-3- azanorborn-5-enes afford versatile cycloadducts and a convenient entry to highly functionalized derivatives

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2613-2620

  Quadrelli, Paolo ^a   Mella, Mariella ^a   Paganoni, Pierangela ^a   Caramella, Pierluigi ^a  

^a UNIVERSITY OF PAVIA   (Italy)

Author keywords

Cycloadditions; Enones; Heterocycles; Oxidations

Indexed keywords

OXIDE;

ARTICLE; CHEMICAL STRUCTURE; HYDROLYSIS; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033865820     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2613::aid-ejoc2613>3.0.co;2-7     Document Type: Article

References (41)

1. P. F. Vogt, M. J. Miller, Tetrahedron 1998, 54, 1317-1348.
2. M. Orena, Methods Org. Chem. (Houben-Weyl), 1995, vol. E21e, p.5547-5587.
3. D. L. Boger, S. M. Weinreb, Hetero Diels-Alder Methodology in Organic Synthesis, Academic Press, San Diego, 1987.
4. G. E. Keck, R. R. Web, J. B. Yates, Tetrahedron 1981, 37, 4007-4016.
5. [5a] G. E. Keck, S. A. Fleming, Tetrahedron Lett. 1978, 4763-4766.
6. [5b] G. E. Keck, S. A. Fleming, D. Nickell, P. Weider, Synth. Commun. 1979, 9, 281-286.
7. [5c] G. E Keck, D. R Romer, J. Org. Chem. 1993, 55, 6083-6089.
8. [6a] J. Streith, A. Defoin, Synthesis 1994, 1107-1117.
9. J. Streith, A. Defoin, Synlett 1996, 189-200 and references therein.
10. D. E. Justice, J. R. Malpass, Tetrahedron 1996, 52, 11977-11994.
11. D. E. Justice, J. R. Malpass, J. Chem. Soc., Perkin Trans. 1 1994, 2559-2564.
12. D. L. Boger, M. Patel, F. Takusagawa, J. Org. Chem. 1985, 50, 1911-1916.
13. W. Adam, N. Bottke, O. Krebs, C. R. Saha-Möller, Eur. J. Org. Chem. 1999, 1963-1965.
14. [11a] P. Quadrelli, A. Gamba Invernizzi, P. Caramella, Tetrahedron Lett. 1996, 37, 1909-1912.
15. [11b]P. Quadrelli, M. Mella, A. Gamba Invernizzi, P. Caramella, Tetrahedron 1999, 55, 10497-10510.
16. P. Caramella, P. Grünanger, 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), John Wiley and Sons, Inc., New York, 1984, vol. 1, p. 291-392.
17. R. Huisgen, 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), John Wiley and Sons, Inc., New York, 1984, vol. 1, p. 1-176.
18. W. Fliege, R. Huisgen, Justus Liebigs Ann. Chem. 1973, 2038-2047.
19. H. Metzger, Methods Org. Chem. (Houben-Weyl), 1968, vol. X/4, pp.112-116.
20. E. Lustig, J. Phys. Chem. 1961, 65, 491-495.
21. G. Bianchi, C. De Micheli, R. Gandolfi, P. Grünanger, P. Vita Finzi, O. Vajna de Pava, J. Chem. Soc., Perkin Trans. 1 1973, 1148-1155.
22. D. A. Brown, W. K. Glass, R. Mageswaran, S. A. Mohammed, Magn. Reson. Chem. 1991, 29, 40-45.
23. W. E. Stewart, T. H. Siddal, Chem. Rev. 1970, 70, 517-551.
24. A. G. Palmer III, J. Cavanagh, P. E. Wright, M. Rance, J. Magn. Reson. 1991, 93, 151-170.
25. O. Exner, Correlation Analysis in Chemistry (Eds.: N. B. Chapman, J. Shorter), Plenum, London, 1978, chapter 10.
26. A. J. H. Klunder, J. Zhu; B. Zwanenburg, Chem. Rev. 1999, 99, 1163-1190.
27. G. Mehta, J. Chandrasekhar, Chem. Rev. 1999, 99, 1437-1467.
28. R. Huisgen, P. H. J. Ooms, M. Mingin, N. L. Allinger, J. Am. Chem. Soc. 1980, 102, 3951-3953.
29. N. G. Rondan, M. N. Paddon-Row, P. Caramella, K. N. Houk, J. Am. Chem. Soc. 1981, 103, 2436-2438.
30. [26a] P. Caramella, N. G. Rondan, M. N. Paddon-Row, K. N. Houk, J. Am. Chem. Soc. 1981, 103, 2438-2440.
31. [26b] K. N. Houk, N. G. Rondan, F. K. Brown, W. L. Jorgensen, J. D. Madura, D. C. Spellmeyer, J. Am. Chem. Soc. 1983, 105, 5980-5988.
32. [27a] A referee points out that the deformation of the double bond of norbornene does not fit with its latest experimental structure, which was determined by microwave spectroscopy in 1977 and shows a planar double bond.
33. [27b] Curiously enough, an experimentally sound structure for the parent norbornene is indeed lacking. In the past 20 years, however, many norbornene derivatives have been investigated experimentally and theoretically and show nonplanar double bonds.
34. [23,27c] High-level calculations agree nicely with the available experimental data and even show an extent of nonplanarity considerably larger than predicted by the low-level STO-3G structures.
35. [27c] - [27b] J. F. Chiang, R. Chiang, K. C. Lu, J. Mol. Struct. 1977, 41, 67-77.
36. [27c] M. C. Holthausen, W. Koch, J. Phys. Chem. 1993, 97, 10021-10027.
37. STO-3G optimizations show significant pyramidalization at the N atoms in anomeric amides. The pyramidalization vanishes, however, at higher levels of theory and after inclusion of the ZPE correction: A. Rank, S. A. Glover, J. Org. Chem. 1996, 61, 2337-2345.
38. A. Rastelli, M. Burdisso, R. Gandolfi, J. Phys. Org. Chem. 1990, 3, 159-173.
39. C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer-Verlag, Heidelberg, 1971.
40. A. Corsico Coda, G. Tacconi, Gazz. Chim. Ital. 1984, 114, 131-132.
41. C. Grundmann, J. M. Dean, J. Org. Chem. 1965, 30, 2809-2812.