2-Vinyl-trans-octahydro-1,3-benzoxazine: Cyclization and 1,3-dipolar cycloaddition of nitrile oxides

Tetrahedron Letters

Volumn 39, Issue 50, 1998, Pages 9121-9124

  Lacoste, Jean Éric ^a   Soucy, Chantal ^a   Rochon, Fernande D ^a   Breau, Livain ^a  

^a UNIVERSITÉ DU QUÉBEC À MONTRÉAL   (Canada)

Author keywords

Asymmetric induction; Benzoxazines; Cycloadditions; Isoxazolines

Indexed keywords

2 VINYL OCTAHYDRO 1,3 BENZOXAZINE; 8 TOSYLAMINOMENTHOL; ACROLEIN DERIVATIVE; BENZOXAZINE DERIVATIVE; ISOXAZOLINE DERIVATIVE; NITRILE OXIDE; PULEGONE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CRYSTAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0032506581     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02061-9     Document Type: Article

References (11)

1. 1. Soucy C.; Lacoste J.-É.; Breau L. Tetrahedron Lett. 1998, 39, 9117-9120.
2. 2. Bernardi, A.; Cardani, S.; Pilati, T.; Poli, G.; Scolastico, C.; Villa, R. J. Org. Chem. 1988, 53, 1600-1607.
3. 3. Eliel E.L.; He X.C. J. Org. Chem. 1990, 55, 2114-2119.
4. 4. Belvisi L.; Gennari C.; Poli G.; Scolastico C.; Salom B.; Vassallo M. Tetrahedron 1992, 48, 19, 3945-3960.
5. 5. All new compounds gave the correct mass spectra and suitable spectroscopic data (IR, NMR, MS). The crystallographic structure for 4a will be published in Acta Crystallographica.
6. 3): 4a: 3.53 (dt, J=11.0 and 4.4 Hz, H-9), 5.95 (dd, J=2.2 and 1.1 Hz, H-2), 4b: 3.81 (dt, J=10.5 and 4.4Hz, H-9), 6.36 (dd, J=2.4 and 1.2Hz, H-2).
7. 2-EtOAc; 8:1:1 gave a mixture of 4a and 4b. Crystallization from pentane afforded pure 4a.
8. 8. Mukerji, S.K.; Sharma, K.K.; Torsell, K.B.G. Tetrahedron 1983, 39, 2231-2235.
9. 3-Ar), 3.03 (dd, J=17.6 and 10.4 Hz, 1H, H-4′), 3.21 (dd, J=17.6 and 6.5 Hz, 1H, H-4′), 3.42 (td, J=11.1 and 4.3 Hz, 1H, H-9), 5.01 (ddd, J=10.4, 8.0 and 6.5 Hz, 1H, H-5′), 5.28 (d, J=8.0 Hz, 1H, H-2), 7.21 (d, J=8.5 Hz, 2H, H-m-Ar), 7.72 (d, J=8.5 Hz, 2H, H-o-Ar).
10. 13 C spectrum of the crude mixture. For isomers 5b and 6b, the ratio was determined by the integration of the signal assigned to C-10; 5b (δ47.19) and 6b (δ48.21).
11. eq protons; the methylene C-4′ is oriented towards C-8. The results of the nOe experiments for 5b and 6b are very similar to those observed for 5a and 6a (e.g. compare 5a and 5b above).