Highly cis- or fraws-selective oxygen to carbon rearrangements of anomerically linked 6-substituted tetrahydropyranyl enol ethers

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 19, 1999, Pages 2665-2667

  Dixon, Darren J ^a   Ley, Steven V ^a   Tate, Edward W ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001322924     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904891j     Document Type: Article

References (20)

1. For excellent reviews see: (a) D. Levy and C. Tang, The Chemistry of C-Glycosides, Pergamon, 1995;
2. (b) M. H. D. Postema, Tetrahedron, 1992,48,8545.
3. M. F. Buffet, D. J. Dixon, G. L. Edwards, S. V. Ley and E. W. Täte, Synlett, 1997, 1055.
4. For related examples see: (a) J. Herscovici, S. Delatre and K. Antonakis, J. Org. Client., 1987, 52, 5691;
5. (b) K. Mikami and H. Kishino, Tetrahedron Lett., 1996, 37, 3705.
6. For related rearrangements at benzylic positions see: (a) J. Wennerberg, L. Eklund, M. Polla and T. Frejd, Client. Commun., 1997,445;
7. (b) J. Wennerberg and T. Frejd, Ada Chem. Scand, 1998,52,95.
8. M. F. Buffet, D. J. Dixon, S. V. Ley and E. W. Täte, Synlett, 1998, 1091.
9. D. J. Dixon, S. V. Ley and E. W. Täte, Synlett, 1998, 1093.
10. D. J. Dixon, S. V. Ley and E. W. Täte, J. Client. Soc., Perkin Trans, l, 1998,3125.
11. For related examples see: (a) M. Takahashi, H. Suzuki, Y. Moro-oka and T. Ikawa, Tetrahedron Lett., 1982, 23, 4031;
12. (b) R. Menicagli, C. Malanga, M. DeH'Innoccnti and L. Lardicci, J. Org. Chem., 1987, 52, 5700;
13. H. Frauenrath and J. Runsink, J. Org. Clicm., 1988,53, 1860;
14. A. Ricci, A. Degl'lnnocenti, A. Capperucci, C. Faggi, G. Seconi and L. Favaretto, Synlett, 1990, 471;
15. (e) D. G. Bourke, D. J. Collins, A. I. Hibbcred and M. D. McLeod, Aust. J. Chem., 1996, 49, 425;
16. (f) M. Sollogoub, J.-M. Mallet and P. Sinay, Tetrahedron Lett., 1998,39,3471.
17. Fresh Tebbe reagent (purchased from Sigma-Aldrich Chemical Co.) is required for this reaction to proceed smoothly. It was found that if an older batch of Tebbe reagent was used the Lewis acidity of the degraded reagent was sufficient to cause some decomposition during the methylenation reaction.
18. 2 requires: C, 74.96; H, 11.60%).
19. For a transition-state discussion of this phenomenon, see P. Deslongchamps, Pure Appl. Client., 1993,65, 1161.
20. Base-induced reversible β-elimination as a method for forming cis-tetrahydropyrans is well-established in synthesis, for example: E. D. Bergman, D. Ginsburg and R. Pappo, Org. React. (N. Y.), 1959,10, 179.