Metalated Epoxides as Carbenoids. Solvent Effect on the Alkyl 1,2-Shift in α-Hydroxy Epoxide Systems

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 3808-3809

  Doris, Eric ^a   Mioskowski, Charles ^a   Dechoux, Luc ^b   Agami, Claude ^b  

^a CEA SACLAY   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000675684     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9805596     Document Type: Article

References (15)

1. For reviews on metalated oxiranes, see: Crandall, J. K.; Apparu, M. Org. React. 1983, 345-443. Satoh, T. Chem. Rev. 1996, 96, 3303-3325. See also: Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946. Agami, C.; Dechoux, L.; Doris, E.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 4071-4074.
2. For reviews on metalated oxiranes, see: Crandall, J. K.; Apparu, M. Org. React. 1983, 345-443. Satoh, T. Chem. Rev. 1996, 96, 3303-3325. See also: Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946. Agami, C.; Dechoux, L.; Doris, E.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 4071-4074.
3. For reviews on metalated oxiranes, see: Crandall, J. K.; Apparu, M. Org. React. 1983, 345-443. Satoh, T. Chem. Rev. 1996, 96, 3303-3325. See also: Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946. Agami, C.; Dechoux, L.; Doris, E.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 4071-4074.
4. For reviews on metalated oxiranes, see: Crandall, J. K.; Apparu, M. Org. React. 1983, 345-443. Satoh, T. Chem. Rev. 1996, 96, 3303-3325. See also: Doris, E.; Dechoux, L.; Mioskowski, C. Tetrahedron Lett. 1994, 35, 7943-7946. Agami, C.; Dechoux, L.; Doris, E.; Mioskowski, C. Tetrahedron Lett. 1997, 38, 4071-4074.
5. Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337-343.
6. Doris, E.; Dechoux, L.; Mioskowski, C. J. Am. Chem. Soc. 1995, 117, 12700-12704.
7. Köbrich, G. Angew. Chem., Int. Ed. Engl. 1972, 11, 473-485.
8. Felix, D.; Wintner, C.; Eschenmoser, A. Org. Synth. 1976, 55, 52-56.
9. 3Li was prepared by halogen-metal exchange, see: Bailey, W. F.; Punzalan, E. R. J. Org. Chem. 1990, 55, 5404-5406.
10. The preferential formation of syn hydroxy epoxide is due to the steric hindrance of the oxirane, which directs nucleophilic addition to the side opposite to the epoxide. See: Sepùlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, II, 233-236. Sepùlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, II, 237-239. Sepùlveda, J.; Soriano, C.; Mestres, R.; Sendra, J. Bull. Soc. Chim. Fr. 1983, II, 240-244.
11. The preferential formation of syn hydroxy epoxide is due to the steric hindrance of the oxirane, which directs nucleophilic addition to the side opposite to the epoxide. See: Sepùlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, II, 233-236. Sepùlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, II, 237-239. Sepùlveda, J.; Soriano, C.; Mestres, R.; Sendra, J. Bull. Soc. Chim. Fr. 1983, II, 240-244.
12. The preferential formation of syn hydroxy epoxide is due to the steric hindrance of the oxirane, which directs nucleophilic addition to the side opposite to the epoxide. See: Sepùlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, II, 233-236. Sepùlveda, J.; Soto, S.; Mestres, R. Bull. Soc. Chim. Fr. 1983, II, 237-239. Sepùlveda, J.; Soriano, C.; Mestres, R.; Sendra, J. Bull. Soc. Chim. Fr. 1983, II, 240-244.
13. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: New York, 1983.
14. McLennan, D. J. In Isotopes in Organic Chemistry; Buncel, E. B., Lee, C. C., Eds.; Elsevier: New York, 1987; Vol. 7, Chapter 6.
15. Dechoux, L.; Doris, E.; Mioskowski, C. Chem. Commun. 1996, 549-550.