Regiospecific access to cyclic allylic alcohols by reductive alkylation of α-alkyloxy-epoxides

Chemical Communications

Volumn , Issue 4, 1996, Pages 549-550

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

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001978952     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/CC9960000549     Document Type: Article

References (12)

1. For a review on epoxide chemistry, see: J. Gorzynski Smith, Synthesis, 1984, 629.
2. (a) For a review on the reactivity of epoxides with strong bases, see: J. K. Crandall and M. Apparu, Org. React. 1983, 29, 345;
3. (b) J. J. Eisch and J. E. Galle, J. Org. Chem., 1990, 55, 4835.
4. E. Doris, L. Dechoux, and C. Mioskowski, Tetrahedron Lett., 1994, 35, 7943 and references cited therein.
5. M. Apparu and M. Barrelle, Tetrahedron, 1978, 34, 1541.
6. E. Doris, L. Dechoux and C. Mioskowski, J. Am. Chem. Soc., 1995, 117, 12700.
7. A. Mordini, E. Ben Rayana, C. Margot and M. Schlosser, Tetrahedron, 1990, 46, 2401. See also ref. 2(a).
8. β-Elimination of ROLi in α-chloro-β-alkyloxy-carbenoid systems have already been reported: J. Villieras, C. Bacquet, J. F. Normant, J. Organomet. Chem., 1975, 97, 355 and references cited therm.
9. For a review on carbenes with neighbouring heteroatoms, see: K. G. Taylor, Tetrahedron, 1982, 38, 2751.
10. Starting epoxy-ketones were prepared according to Eschenmoser's procedure: D. Felix, C. Wintner and A. Eschenmoser, Org. Synth., 1976, 55, 52.
11. The epoxy-alcohol was obtained regiospecifically with excellent diastereotacial selectivity (> 20: 1). The stereochemistry of the epoxy-alcohol moiety was confirmed by MCPBA epoxidation of the corresponding substituted allylic alcohol. See: T. Itoh, K. Jitsukawa, K. Kaneda, S. Teranishi, J. Am Chem. Soc., 1979, 101, 159.
12. N. C. Burua, J. C. Sarma, R. P. Sharma and J. N. Barua, Chem. Ind., 1982, 956.