The first regio- and diastereoselective synthesis of homochiral perhydroimidazoisoxazoles via the 1,3-dipolar cycloaddition of imidazoline 3-oxides with (1S)-(-)-β-pinene

Tetrahedron Asymmetry

Volumn 12, Issue 10, 2001, Pages 1463-1467

  Coşkun, Necdet ^a   Tat, Fatma Tirli ^a   Güven, Özden Özel ^b  

^a ULUDAG UNIVERSITY   (Turkey)

^b ZONGULDAK KARAELMAS UNIVERSITY   (Turkey)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0038326063     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(01)00270-1     Document Type: Article

References (13)

1. March, P.; Figueredo, M.; Font, J.; Gallagher, T.; Milan, S. J. Chem. Soc., Chem. Commun. 1995, 2097-2098.
2. Goti, A.; Fedi, V.; Nannelli, L.; DeSarlo, F.; Brandi, A. Synlett 1997, 5, 577.
3. Cicchi, S.; Crea, S.; Goti, A.; Brandi, A. Tetrahedron: Asymmetry 1997, 8, 293-301.
4. (a) Coşkun, N. Tetrahedron Lett. 1997, 38, 2299-2302
5. (b) Coşkun, N. Tetrahedron 1997, 53, 13873-13882.
6. Coşkun, N.; Ay, M. Heterocydes 1998, 48, 537-544.
7. The adducts of imidazoline 3-oxides 1 with DMAD were proved to have cis structure by X-ray analysis: Coşkun, N.; Tat, F. T.; Güven, Ö. Ö.; Ülkü, D.; Arici, C. Tetrahedron Lett. 2000, 41, 5407-5409; Coşkun, N.; Tat, F. T.; Güven, Ö. Ö. Tetrahedron 2001, 57, 3413-3417.
8. The adducts of imidazoline 3-oxides 1 with DMAD were proved to have cis structure by X-ray analysis: Coşkun, N.; Tat, F. T.; Güven, Ö. Ö.; Ülkü, D.; Arici, C. Tetrahedron Lett. 2000, 41, 5407-5409; Coşkun, N.; Tat, F. T.; Güven, Ö. Ö. Tetrahedron 2001, 57, 3413-3417.
9. Alencar, K. G.; Filho, U. F. L.; Vasconcellos, M. L. A. A.; Costa, P. R. R. Synth. Commun. 2000, 30, 455-468.
10. Dumas, F.; Alencar, K.; Mahuteau, J.; Barbero, M. J. L.; Miet, C.; Gerard, F.; Vasconcellos, M. L. A. A; Costa, P. R. R. Tetrahedron: Asymmetry 1997, 8, 579-583.
11. The imidazole forms from the thermal dehydration of the corresponding imidazoline 3-oxide.
12. AB= 8.57, C-4), 5.54 (1H, s, C-6), 6.39 (2H, d, J=8.97, N-Ph ortho), 6.73 (2H, d, J=8.97, N-phenyl meta H), 7.00 (6H, m, C-3a and C-6 phenyl meta and para H), 7.20 (2H, m, C-6 phenyl ortho H), 7.33 (2H, m C-3a phenyl ortho H)
13. Coşkun, N.; Asutay, A. Chim. Acta Turc. 1997, 25, 69-72.