Substituted alkenediols by alkylative double ring opening of dihydrofuran and dihydropyran epoxides

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3401-3403

  Hodgson, David M ^a   Stent, Matthew A H ^a   Wilson, Francis X ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001072368     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016638c     Document Type: Article

References (29)

1. Erden, I. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon Press: Oxford, 1996; Vol. 1A, pp 97-171.
2. (a) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4526-4257.
3. (b) Crandall, J. K.; Lin, L.-H. C. J. Am. Chem. Soc. 1967, 89, 4527-4528.
4. (c) Crandall, J. K.; Apparu, M. Org. React. (N.Y.) 1983, 29, 345-443.
5. Reviews: (a) Satoh, T. Chem. Rev. 1996, 96, 3303-3325.
6. (b) Doris, E.; Dechoux, L.; Mioskowski, C. Synlett 1998, 337-343.
7. Dechoux, L.; Doris, E.; Mioskowski, C. Chem. Commun. 1996, 549-550.
8. (a) Hodgson, D. M.; Lee, G. P.; Marriott, R. E.; Thompson, A. J.; Wisedale, R.; Witherington, J. J. Chem. Soc., Perkin Trans. 1 1998, 2151-2161.
9. (b) Hodgson, D. M.; Robinson, L. A. Chem. Commun. 1999, 309-310.
10. (c) Hodgson, D. M.; Cameron, I. D. Org. Lett. 2001, 3, 441-444.
11. (d) Hodgson, D. M.; Cameron, I. D.; Christlieb, M.; Green, R.; Lee, G. P.; Robinson, L. A. J. Chem. Soc., Perkin Trans. 1 2001, 2161-2174.
12. 3,4-Epoxytetrahydrofuran 5 is commercially available from Acros Organics. It can be prepared by epoxidation of widely available 2,5-dihydrofuran (Barili, P. L.; Berti, G.; Mastrorilli, E. Tetrahedron 1993, 49, 6263-6276).
13. 2 162.1494, found 162.1494.
14. Calaza, M. I.; Paleo, M. R.; Sardina, F. J. J. Am. Chem. Soc. 2001, 123, 2095-2096.
15. Alkenediols 8, 10, and 11 are known compounds (Schulte-Elte, K. H.; Muller, B. L.; Pamingle, H. Helv. Chim. Acta 1979, 62, 816-829).
16. Fleming, I.; Dunoguès, J.; Smithers, R. Org. React. (N.Y.) 1989, 37, 57-575.
17. 2O, 0 °C, 3 h, 73%.
18. Hopkins, M. H.; Overman, L. E.; Rishton, G. M. J. Am. Chem. Soc. 1991, 113, 5354-5365.
19. Yang, D.; Wong, M.-K.; Yip, Y.-C. J. Org. Chem. 1995, 60, 3887-3889.
20. Prepared via cycloaddition of furan with vinylidene carbonate: de Micheli, C.; de Amici, M.; Grana, E.; Zonta, F.; Giannella, M.; Piergentili, A. Farmaco 1993, 48, 1333-1348.
21. 2, 25 °C, 16 h) gave epoxides 18 and 19 (18:19, 1:2) in 75% yield.
22. 1H NOESY studies on both isomers: diol 20 showed strong correlations between the olefinic proton and the protons α-OH, while 21 showed correlations between the olefinic proton and the butyl chain only.
23. (a) Kasatkin, A. N.; Whitby, R, J. Tetrahedron Lett. 2000, 41, 5275-5280.
24. (b) Boche, G.; Lohrenz, J. C. W. Chem. Rev. 2001, 101, 697-756.
25. Assuming an early transition state for the elimination, then the required anti alignment of bonds is easily achieved (Scheme 9). Syn elimination is not possible.
26. 2Si) ethers all underwent decomposition. The failure of noncyclic substrates to react via oxiranyl anion chemistry has been previously observed (refs 4 and 22).
27. Berti, G.; Catelani, G.; Ferretti, M.; Monti, L. Tetrahedron 1974, 30, 4013-4020.
28. 2, 25 °C, 16 h, 35% yield) of the corresponding dihydropyran (Booth, H.; Khedhair, K. A.; Readshaw, S. A. Tetrahedron 1987, 43, 4699-4723).
29. Doris, E.; Dechoux, L.; Mioskowski, C. J. Am. Chem. Soc. 1995, 117, 12700-12704.