Radical fragmentation of β-hydroxy azides. Synthesis of chiral nitriles

Journal of Organic Chemistry

Volumn 62, Issue 26, 1997, Pages 8974-8975

  Hernández, Rosendo ^a   León, Elisa I ^a   Moreno, Pilar ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84855648259     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo971836w     Document Type: Article

References (32)

1. (a) Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774.
2. (b) Armas, P.; Francisco, C. G.; Suárez, E J. Am. Chem. Soc. 1993, 115, 8865-8866.
3. (c) Armas, P.; Francisco, C. G.; Suárez, E. Tetrahedron Lett. 1993, 34, 7331-7334.
4. (d) Francisco, C. G.; González, C. C.; Suárez, E. Tetrahedron Lett. 1996, 37, 1687-1690.
5. (e) Francisco, C. G.; Freire, R.; González, C. C.; Suárez, E. Tetrahedron: Asymmetry 1997, 8, 1971-1974.
6. (a) The Chemistry of the Cyano Group; Rappoport, Z., Ed.; Interscience: New York, 1970.
7. (b) Arseniyadis, S.; Kyler, K. S.; Watt, D. S. In Organic Reactions; Dauben, W. G., Ed.; John Wiley: New York, 1984; Vol. 31, pp 1-374.
8. (a) Brennam, B. A.; Alms, G.; Nelson, M. J.; Durney, L. T.; Scarrow, R. C. J. Am. Chem. Soc. 1996, 118, 9194-9195.
9. (b) Taylor, S. K.; Chmiel, H. H.; Simons, L. J.; Vyvyan, J. R. J. Org. Chem. 1996, 61, 9084-9085.
10. (c) Maddrell, S. J.; Turner, N. J.; Kerridge, A.; Willetts, A. J.; Crosby, J. Tetrahedron Lett. 1996, 37, 6001-6004.
11. Bishop, R. In Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Eds.; Pergamon Press: Oxford, 1991; Vol. 6, pp 261-300.
12. Zbiral, E.; Nestler, G.; Kischa, K. Tetrahedron 1970, 26, 1427-1434.
13. (b) Zbiral, E.; Nestler, G. Tetrahedron 1970, 26, 2945-2951.
14. (c) Ehrenfreund, J.; Zbiral, E. Tetrahedron 1972, 28, 1697-1704.
15. Shimizu, I.; Fujita, M.; Nakajima, T.; Sato, T. Synlett 1997, 887-888.
16. Fürstner, A.; Praly, J.-P. Angew. Chem., Int. Ed. Engl. 1994, 33, 751-753.
17. Boche, G. In Stereoselective Synthesis, Methods of Organic Chemistry (Houben-Weyl); Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E 21-9; pp 5190-5221.
18. Grundler, G.; Schmidt, R. R. Liebigs Ann. Chem. 1984, 1826-1847.
19. (a) Lemieux, R. U.; Ratcliffe, R. M. Can. J. Chem. 1979, 57, 1244-1251.
20. (b) Lin, C.-H.; Sugai, T.; Halcomb, R. L.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 10138-10145.
21. (c) Bemiller, J. N.; Blazis, V. J.; Myers, R. W. J. Carbohydr. Chem. 1990, 9, 39-57.
22. Toyokuni, T.; Cai, S.; Dean, B. Synthesis 1992, 1236-1238.
23. (a) Lee, J. B.; Nolan, T. J. Tetrahedron 1967, 23, 2789-2794.
24. (b) Eitelman, S. J.; Hall, R. H.; Jordaan, A. J. Chem. Soc., Perkin Trans. 1 1978, 595-600.
25. (a) Czernecki, S.; Ayadi, E. Can. J. Chem. 1995, 73, 343-350.
26. (b) Czernecki, S.; Ayadi, E. J. Org. Chem. 1994, 59, 8256-8260.
27. (c) Czernecki, S.; Ayadi, E.; Randriamandimby, D. J. Chem. Soc., Chem. Commun. 1994, 35-36.
28. (d) Czernecki, S.; Randriamandimby, D. Tetrahedron Lett. 1993, 34, 7915-7916.
29. (e) Santoyo-González, F.; Calvo-Flores, F. G.; García-Mendoza, P.; Hernández-Mateo, F.; Isac-García, J.; Robles-Díaz, R. J. Org. Chem. 1993, 58, 6122-6125.
30. (f) Paulsen, H.; Sumfleth, B. Chem Ber. 1979, 112, 3203-3213.
31. Griesbeck, A. G.; Hundertmark, T.; Steinwascher, J. Tetrahedron Lett. 1996, 46, 8367-8370.
32. The Chemistry of the Azido Group; Patai, S., Ed.; Interscience: New York, 1971; pp 348, 441.