Stability of electron deficient activated nitronates under neutral and Lewis acid catalyzed conditions. Facile nitronate cycloaddition reactions to the magnesium alkoxides of allylic alcohols leading to isoxazolidines and isoxazolines

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8865-8868

  Kanemasa, Shuji ^a   Kaga, Shinsuke ^a   Wada, Eiji ^a  

^a KYUSHU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALCOHOL; BORON DERIVATIVE; ISOXAZOLIDINE DERIVATIVE; ISOXAZOLINE DERIVATIVE; MAGNESIUM DERIVATIVE; NITRILE; NITRILE OXIDE; NITROALKANE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032569897     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01902-9     Document Type: Article

References (28)

1. 1 Tufariello, J.J.; Nitrone as Chapt. 9 of 1,3-Dipolar Cycloaddition Chemistry, Padwa, A. Ed.; A Wiley-Interscience Publication: New York, 1984; Vol. 2, pp 83-168.
2. 2 Breuer, E.; Aurich, H. G.; Nielsen, A.; Nitrones, nitronates and nitroxides, Patai, S.; Rappoport, Z. Ed.; John Wiley & Sons: Chichester, 1989; Chapts. 2 and 3, pp 139-312.
3. 3 (a) Boron trifluoride catalyzes the cycloaddition of nitronic esters. Levina, I. S.; Mortikova, E. I.; Kamernitzky, A. V. Synthesis, 1974, 562-563.
4. (b) Torssell, K. B. G.; Hazell, A. C.; Hazell, R. G. Tetrahedron 1985, 41, 5569-5576.
5. (c) Tartakovskii, V. A.; Savost'yanova, I. A.; Novikov, S. S. Zh. Org. Khim., 1968, 4, 240-243.
6. 4 Wade, P. A.; Amin, N. V.; Yen, H.-K.; Price, D. T.; Huhn, G. F. J. Org. Chem. 1984, 49, 4595-4601.
7. 5 (a) Jensen, K. B.; Gothelf, K. V.; Jørgensen, K. A. Helv. Chim. Acta 1997, 80, 2039-2046.
8. (b) Jensen, K. B.; Gothelf, K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1997, 62, 2471-2477.
9. (c) Gothelf, K. V.; Jørgensen, K. A. Acta Chem. Scand. 1996, 50, 652.
10. (d) Gothelf, K. V.; Thomsen, I.; Jørgensen, K. A. J. Am. Chem. Soc. 1996, 118, 59-64.
11. (e) Gothelf, K. V.; Jørgensen, K. A. J. Org. Chem. 1994, 59, 5687-5991
12. 6 Gothelf K. V.; Hazell, R. G.; Jørgensen, K. A. J. Org. Chem. 1996, 61, 346-355.
13. 7 Sanchez-Blanco, A. I.; Gothelf, K. V.; Jørgensen, K. A. Tetrahedron Lett. 1997, 38, 7923-7926.
14. 8 Hori, K.; Kodama, H.; Ohta, T. Furukawa, I. Tetrahedron Lett. 1996, 37, 5947-5950.
15. 9 (a) Kobayashi, S.; Kawamura, M. J. Am. Chem. Soc. 1998, 120, 5840-5841.
16. (b) Kobayashi, S.; Akiyama, R.; Kawamura, M.; Ishitani, H. Chem. Lett. 1997, 1039-1040.
17. 10 (a) Seerden, J.-P. G.; Boeren, M. M. M.; Scheeren, H. W. Tetrahedron 1997, 53, 11843-11852.
18. (b) Seerden, J.-P. G.; Scholte op Reimer, A. W. A.; Scheeren, H. W. Tetrahedron Lett. 1994, 35, 4419-4422.
19. 11 Ukaji, Y.; Taniguchi, K.; Sada, K.; Inomata, K. Chem. Lett. 1997, 547-548.
20. 12 Huisgen, R.; Seidle, H.; Brüning, I. Chem. Ber. 1969, 102, 1102-1116.
21. 13 Kornblum, K.; Brown, R. A. J. Am. Chem. Soc. 1964, 86, 2681-2687.
22. 14 The irreversible sigmatropic fragmentation of nitronates is known as an important preparative method of oximes (Ref. 2).
23. 1H NMR spectrum. Deuteriochloroform was filtered through a short column packed with basic alumina and then used for the stability test.
24. 17 For the magnesium ion mediated nitrone cycloadditions to allylic alcohols, see: Kanemasa, S.; Tsuruoka, T.; Wada, E. Tetrahedron Lett. 1993, 34, 87-90.
25. 3) Z-isomer: δ = 51.95, 52.51, 105.82, and 159.60; E-isomer: δ = 52.13, 53.28, 104.23, and 160.37.
26. 19 Greé, R.; Carrié, R. Bull. Soc. Chim. Fr., 1975, 1314-1318.
27. 20 The O-methyl substituent of nitronate Z-2 is located close to the N-oxide oxygen due to the steric hindrance to the adjacent methoxycarbonyl group so that the fragmentation reaction may be easier.
28. 21 Interaction of Lewis acid with nitrones has been reported (Kanemasa, S.; Uemura, T.; Wada, E. Tetrahedron Lett. 1992, 33, 7889-7892).