Intramolecular 1,3-Dipolar Cycloaddition of Nitrones to Allylsilanes

Synlett

Volumn 1996, Issue 12, 1996, Pages 1215-1217

  Arnold, Wolf ^a   Mohr, Peter ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001925987     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5702     Document Type: Article

References (21)

1. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, Gazz. Chim. Ital. 1989, 119, 253; A. Padwa and A. M. Shoffstall, "Advances in Cycloaddition", Vol. 2, D. P. Curran Ed., JAI Press Inc., London, 1990; for recent examples see e. g. M. E. Jung, B. T. Vu, J. Org. Chem. 1996, 61, 4427; H. G. Aurich, M. Geiger, Ch. Gentes, H. Köster, Tetrahedron Lett. 1996, 37, 841.
2. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, Gazz. Chim. Ital. 1989, 119, 253; A. Padwa and A. M. Shoffstall, "Advances in Cycloaddition", Vol. 2, D. P. Curran Ed., JAI Press Inc., London, 1990; for recent examples see e. g. M. E. Jung, B. T. Vu, J. Org. Chem. 1996, 61, 4427; H. G. Aurich, M. Geiger, Ch. Gentes, H. Köster, Tetrahedron Lett. 1996, 37, 841.
3. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, Gazz. Chim. Ital. 1989, 119, 253; A. Padwa and A. M. Shoffstall, "Advances in Cycloaddition", Vol. 2, D. P. Curran Ed., JAI Press Inc., London, 1990; for recent examples see e. g. M. E. Jung, B. T. Vu, J. Org. Chem. 1996, 61, 4427; H. G. Aurich, M. Geiger, Ch. Gentes, H. Köster, Tetrahedron Lett. 1996, 37, 841.
4. R. Annunziata, M. Cinquini, F. Cozzi, L. Raimondi, Gazz. Chim. Ital. 1989, 119, 253; A. Padwa and A. M. Shoffstall, "Advances in Cycloaddition", Vol. 2, D. P. Curran Ed., JAI Press Inc., London, 1990; for recent examples see e. g. M. E. Jung, B. T. Vu, J. Org. Chem. 1996, 61, 4427; H. G. Aurich, M. Geiger, Ch. Gentes, H. Köster, Tetrahedron Lett. 1996, 37, 841.
5. P. DeShong, J. M. Leginus, S. W. Lander, Jr., J. Org. Chem. 1986, 51, 574.
6. P. Mohr, Tetrahedron Lett. 1995, 36, 7221, and references cited therein.
7. D. M. Bailey, R. E. Johnson, J. Org. Chem. 1970, 35, 3574.
8. All yields refer to isolated and chromatographically purified material and are not optimized.
9. I. Fleming, I. Paterson, Synthesis 1979, 446; D. Seyferth, K. R. Wursthorn, R. E. Mammarella, J. Org. Chem. 1977, 42, 3104.
10. I. Fleming, I. Paterson, Synthesis 1979, 446; D. Seyferth, K. R. Wursthorn, R. E. Mammarella, J. Org. Chem. 1977, 42, 3104.
11. P. DeShong, J. M. Leginus, J. Org. Chem. 1984, 49, 3421.
12. 3), however, they begin slowly to cyclize.
13. D. W. Hart, T. F. Blackburn, J. Schwartz, J. Am. Chem. Soc. 1975, 97, 679.
14. Lactol 13 exists, according to NMR, to a significant extent as hydroxy-aldehyde. This behaviour is reflected in a substantially faster Wittig reaction than observed with the six-membered lactol 4.
15. S. V. Ley, J. Norman, W. P. Griffith, S. P. Marsden, Synthesis 1994, 639.
16. In contrast, compound 4, prevailing exclusively as lactol (cf. note 10), afforded under identical conditions only silylated lactol.
17. S. K. Chiu, P. E. Peterson, Tetrahedron Lett. 1980, 21, 4047.
18. 3, 400MHz) δ 0.05 (s, 9H), 0.59 (dd, J=14, 3.2 Hz, 1H), 0.71 (dd, J=14, 11.6 Hz, 1H), 0.84 (s, 9H), 0.95-1.10 (m, 3H), 1.25 (m, 1H), 1.75 (m, 2H), 1.85 (m, 1H), 2.10 (m, 1H), 2.30 (m, 1H), 3.86 (d, J=13.2 Hz, 1H), 3.97 (d, J=13.2 Hz, 1H), 4.26 (m, 1H), 7.23-7.31 (m, 3H), 7.39 (d, J=8 Hz, 2H); MS m/z 359, 344, 302 (base peak).
19. M. E. Jung, B. T. Vu, Tetrahedron Lett. 1996, 37, 451; A. L. Parrill, D. P. Dolata, ibid 1994, 35, 7319.
20. M. E. Jung, B. T. Vu, Tetrahedron Lett. 1996, 37, 451; A. L. Parrill, D. P. Dolata, ibid 1994, 35, 7319.
21. H. G. Aurich, F. Biesemeier, Synthesis 1995, 1171.