Direct enantioselective approach to oxazolo[4,5-e]isoindoles from [(S)R]-1-aminosubstituted-4-(p-tolylsulfinyl)-1,3-butadienes

Tetrahedron Asymmetry

Volumn 10, Issue 18, 1999, Pages 3473-3477

  Blasco, S ^a   Carreno M C ^a   Cid, M B ^a   Garcia Ruano J L ^a   Martin M R ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ISOINDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033435121     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00356-0     Document Type: Article

References (20)

1. For reviews, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717.
2. (b) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. Tetrahedron: Asymmetry 1997, 8, 1339.
3. Cid, M. B.; García Ruano, J. L. In Topics in Current Chemistry. Organosulfur Chemistry; Page, P. C. B., Ed.; Springer: Berlin, in press. For more recent references see: Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontaine, J. A.; Montero, C.; McCulley, D. J.; Rubio, M. B.; Ventura, M. P.; Weers, H.; Fernández de la Pradilla, R.; Castro, S.; Dorado, R.; Morente, M. J. Org. Chem. 1997, 62, 6326.
4. Cid, M. B.; García Ruano, J. L. In Topics in Current Chemistry. Organosulfur Chemistry; Page, P. C. B., Ed.; Springer: Berlin, in press. For more recent references see: Paley, R. S.; Dios, A. de; Estroff, L. A.; Lafontaine, J. A.; Montero, C.; McCulley, D. J.; Rubio, M. B.; Ventura, M. P.; Weers, H.; Fernández de la Pradilla, R.; Castro, S.; Dorado, R.; Morente, M. J. Org. Chem. 1997, 62, 6326.
5. (d) Fernández de la Pradilla, R.; Martínez, M. V.; Montero, C.; Viso, A. Tetrahedron Lett. 1997, 38, 7773.
6. For recent references see: (d) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Bruno, G.; Giannetto, P.; Panzarlorto, M. Tetrahedron: Asymmetry 1997, 8, 2989.
7. (e) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Panzarlorto, M.; Rizzo, S. Tetrahedron: Asymmetry 1998, 9, 1577.
8. (f) Fernández de la Pradilla, R.; Montero, C.; Viso, A. Chem. Commun. 1998, 9, 409.
9. (g) Adams, H.; Anderson, J. C.; Bell, R.; Jones, D. N.; Peel, M. R.; Tomkinson, N. C. O. J. Chem. Soc., Perkin Trans. 1 1998, 3967.
10. (h) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. J. Org. Chem. 1999, 64, 2114.
11. Overman, L. E.; Petty, C. B.; Ban, T.; Huang, G. J. Am. Chem. Soc. 1983, 105, 6335.
12. Arce, E.; Carreño, M. C.; Cid, M. B.; García Ruano, J. L. J. Org. Chem. 1994, 59, 3421.
13. Carreño, M. C.; Cid, M. B.; García Ruano, J. L. Tetrahedron: Asymmetry 1996, 7, 2151.
14. Carreño, M. C.; Cid, M. B.; García Ruano, J. L. Santos, M. Tetrahedron Lett. 1998, 39, 1405.
15. Fisher, M. J.; Hehre, W. J.; Kahn, S. D. Overman, L. E. J. Am. Chem. Soc. 1988, 110, 4625.
16. For a review see: (a) Hofmann, R. W. Chem. Rev. 1989, 89, 1841. For a study of the role of 1,3-allylic strain in the stereoselectivity of 2-methyl-1-substituted dienes see: Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190.
17. For a review see: (a) Hofmann, R. W. Chem. Rev. 1989, 89, 1841. For a study of the role of 1,3-allylic strain in the stereoselectivity of 2-methyl-1-substituted dienes see: Adam, W.; Gläser, J.; Peters, K.; Prein, M. J. Am. Chem. Soc. 1995, 117, 9190.
18. (a) Bickart, P.; Carson, F. W.; Jacobus, J.; Miller, E. G.; Mislow, K. J. Am. Chem. Soc. 1968, 90, 4869.
19. (b) Tang, R.; Mislow, K. J. Am. Chem. Soc. 1970, 92, 2100.
20. (c) Evans, D. A.; Andrews, G. C. Acc. Chem. Res. 1974, 7, 147.