Selective ring opening of silylated vinyloxiranes and reactivity of azido-alcohols

Arkivoc

Volumn 2007, Issue 5, 2007, Pages 277-292

  Marié, Jean Charles ^a   Courillon, Christine ^a   Malacria, Max ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

Azide; Chemoselectivity; Nucleophilic ring opening; Oxirane; Rearrangement; Silicon

Indexed keywords

EID: 33847658785     PISSN: 1551-7012     EISSN: 14246376     Source Type: Journal    
DOI: 10.3998/ark.5550190.0008.521     Document Type: Article

References (20)

1. Mulzer, J. In Stereosel. Synth. Ottow, E.; Schoellkopf, K.; Schulz, B.-G., Eds.; Springer: Berlin, 1993; 37.
2. Marié, J.-C.; Courillon, C.; Malacria, M. Eur. J. Org. Chem. 2006, 463.
3. Marié, J.-C.; Courillon, C.; Malacria, M. Tetrahedron 2003, 59, 9759.
4. Marié, J.-C.; Courillon, C.; Malacria, M. Synlett 2002, 553.
5. Padwa, A.; Murphee, S. S. Arkivoc 2006, (iii), 6.
6. Chakraborty, T. K.; Laxman, P. Tetrahedron Lett. 2002, 43, 2645;
7. (b) Wipf, P.; Fritch, P. C. J. Org. Chem. 1994, 59, 4875;
8. (c) Sabitha, G.; Babu, S. R.; Reddy, M. S. K.; Yadav, J. S. Synthesis, 2002, 2254;
9. (d) Sabitha, G.; Babu, R. S.; Rajkumar, M.; Yadav, J. S. Org. Lett., 2002, 4, 343.
10. Marion, F.; Calvet, S.; Marié, J.-C.; Courillon, C.; Malacria, M. Eur. J. Org. Chem. 2006, 453.
11. Gilloir, F.; Malacria, M. Tetrahedron Lett. 1992, 33, 3849.
12. Chakraborty, T. K.; Reddy, G. V. Tetrahedron Lett. 1990, 31, 1335.
13. Chakraborty, T. K.; Reddy, G. V. Tetrahedron Lett. 1991, 32, 679.
14. Regueiro-Ren, A.; Borzilleri, R. M.; Zheng, X.; Kim, S.-H.; Johnson, J. A.; Fairchild, C. R.; Lee, F. Y. F.; Long, B. H.; Vite, G. D. Org. Lett. 2001, 3, 2693.
15. Manis, P. A.; Rathke, M. W. J. Org. Chem. 1980, 45, 4952.
16. Jarvis, B. B.; Nicholas, P. E. J. Org. Chem. 1979, 44, 2951.
17. Jarvis, B. B.; Nicholas, P. E. J. Org. Chem. 1980, 45, 2265.
18. Canas, M.; Poch, M.; Verdaguer, X.; Moyano, A.; Pericas, M. A.; Riera, A. Tetrahedron Lett. 1991, 32, 6931.
19. Le Bideau, F.; Gilloir, F.; Nilsson, Y.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1995, 36, 1641.
20. (b) Le Bideau, F.; Gilloir, F.; Nilsson, Y.; Aubert, C.; Malacria, M. Tetrahedron 1996, 52, 7487.