Cascade reaction of 6-deoxy-6-iodohexopyranosides promoted by samarium diiodide: A new ring contraction of carbohydrate derivatives

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6488-6489

  Chiara, Jose Luis ^a   Martínez, Sonia ^a   Bernabé, Manuel ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; CATALYSIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029798349     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961116+     Document Type: Article

References (37)

1. For excellent accounts on the subject, see the recent Chem. Rev. thematic issue on "Frontiers in Organic Chemistry": Chem. Rev. 1996, 96 (1).
2. For excellent accounts on the subject, see the recent Chem. Rev. thematic issue on "Frontiers in Organic Chemistry": Chem. Rev. 1996, 96 (1).
3. For a recent review, see: Molander, G. A. Chem. Rev. 1996, 96, 307-338.
4. (a) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1996, 118, 4059-4071.
5. (b) Molander, G. A.; Harris, C. R. J. Am. Chem. Soc. 1995, 117, 3705-3716.
6. (c) Molander, G. A.; McKie, J. A. J. Org. Chem. 1995, 60, 872-882 and references cited therein.
7. (d) Enholm, E. J.; Jiang, S.; Abboud, K. J. Org. Chem. 1993, 58, 4061-4069 and references cited therein.
8. (e) Curran, D. P.; Wolin, R. L. Wolin, R. L. Synlett 1991, 317-318.
9. (f) Curran, D. P.; Fevig, T. L.; Totleben, M. J. Synlett 1990, 773-774.
10. For a recent highlight on ring contractions in carbohydrates, see: Redlich, H. Angew. Chem., Int. Ed. Engl. 1994, 33, 1345-1347.
11. 2, see: Chénedé, A.; Pothier, P.; Sollogoub, M.; Fairbanks, A. J.; Sinay, P. J. Chem. Soc., Chem. Commun. 1995, 1373-1374.
12. Originally described with Zn or butyllithium by: (a) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016. For modified procedures, see: (b) Fürstner, A.; Baumgartner, J.; Jumbam, D. N. J. Chem. Soc., Perkin Trans, 1 1993, 131-138 and references cited therein. For previous reports on ring scissions of cyclic β-halo ethers promoted by samarium diiodide, see: (c) Crombie, L.; Rainbow, L. J. J. Chem. Soc., Perkin Trans. 1 1994, 673-687. (d) Tetrahedron Lett. 1988, 29, 6517-6520.
13. Originally described with Zn or butyllithium by: (a) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016. For modified procedures, see: (b) Fürstner, A.; Baumgartner, J.; Jumbam, D. N. J. Chem. Soc., Perkin Trans, 1 1993, 131-138 and references cited therein. For previous reports on ring scissions of cyclic β-halo ethers promoted by samarium diiodide, see: (c) Crombie, L.; Rainbow, L. J. J. Chem. Soc., Perkin Trans. 1 1994, 673-687. (d) Tetrahedron Lett. 1988, 29, 6517-6520.
14. Originally described with Zn or butyllithium by: (a) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016. For modified procedures, see: (b) Fürstner, A.; Baumgartner, J.; Jumbam, D. N. J. Chem. Soc., Perkin Trans, 1 1993, 131-138 and references cited therein. For previous reports on ring scissions of cyclic β-halo ethers promoted by samarium diiodide, see: (c) Crombie, L.; Rainbow, L. J. J. Chem. Soc., Perkin Trans. 1 1994, 673-687. (d) Tetrahedron Lett. 1988, 29, 6517-6520.
15. Originally described with Zn or butyllithium by: (a) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016. For modified procedures, see: (b) Fürstner, A.; Baumgartner, J.; Jumbam, D. N. J. Chem. Soc., Perkin Trans, 1 1993, 131-138 and references cited therein. For previous reports on ring scissions of cyclic β-halo ethers promoted by samarium diiodide, see: (c) Crombie, L.; Rainbow, L. J. J. Chem. Soc., Perkin Trans. 1 1994, 673-687. (d) Tetrahedron Lett. 1988, 29, 6517-6520.
16. (a) Fevig, T. L.; Elliot, R. L.; Curran, D. P. J. Am. Chem. Soc. 1988, 110, 5064-5067.
17. (b) Enholm, E. J.; Trivellas, A. Tetrahedron Lett. 1989, 30, 1063-1066.
18. (c) Baldwin, J. E.; Turner, S. C. M.; Moloney, M. G. Tetrahedron 1994, 50, 9411-9424.
19. All new compounds showed correct microanalytical and spectroscopic data.
20. 2.
21. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Parkin Trans, 1 1980, 2866-2869.
22. Whistler, R. L.; Anisuzzaman, A. K. M. Methods Carbohydr. Chem. 1980, 8, 227-231.
23. 1H NMR and 2D NOESY studies (see the supporting information).
24. A similar effect of temperature on the extent of competing dehalogenation vs dealkoxyhalogenation has been previously observed in the reaction of halo sugars with metal-graphite reagents: Fürstner, A.; Koglbauer, U.; Weidmann, H. J. Carbohydr. Chem. 1990, 9, 561-570. Fürstner, A.; Jumbam, D.; Teslic, J.; Weidmann, H. J. Org. Chem. 1991, 56, 2213-2217.
25. A similar effect of temperature on the extent of competing dehalogenation vs dealkoxyhalogenation has been previously observed in the reaction of halo sugars with metal-graphite reagents: Fürstner, A.; Koglbauer, U.; Weidmann, H. J. Carbohydr. Chem. 1990, 9, 561-570. Fürstner, A.; Jumbam, D.; Teslic, J.; Weidmann, H. J. Org. Chem. 1991, 56, 2213-2217.
26. 6b
27. 2. Similar 1,5-hydrogen migrations in radical intermediates from benzylated sugar derivatives have been reported before: (a) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem B. J. Am. Chem. Soc. 1989, 111, 783-785. (b) Martin, O. R.; Xie, F.; Kakarla, R.; Benhamza, R. Synlett 1993, 165-167. (c) Barbaud, C.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron 1995, 51, 9063-9078 (see also ref 6b).
28. 2. Similar 1,5-hydrogen migrations in radical intermediates from benzylated sugar derivatives have been reported before: (a) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem B. J. Am. Chem. Soc. 1989, 111, 783-785. (b) Martin, O. R.; Xie, F.; Kakarla, R.; Benhamza, R. Synlett 1993, 165-167. (c) Barbaud, C.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron 1995, 51, 9063-9078 (see also ref 6b).
29. 2. Similar 1,5-hydrogen migrations in radical intermediates from benzylated sugar derivatives have been reported before: (a) Liotta, L. J.; Bernotas, R. C.; Wilson, D. B.; Ganem B. J. Am. Chem. Soc. 1989, 111, 783-785. (b) Martin, O. R.; Xie, F.; Kakarla, R.; Benhamza, R. Synlett 1993, 165-167. (c) Barbaud, C.; Bols, M.; Lundt, I.; Sierks, M. R. Tetrahedron 1995, 51, 9063-9078 (see also ref 6b).
30. A similar trans-directing effect of adjacent alkoxy groups has been observed in intramolecular pinacol coupling reactions promoted by samarium diiodide, and it was attributed to steric and/or electrostatic interactions involving the ketyl radical anion and the alkoxy substituent: Chiara, J. L.; Cabri, W.; Hanessian, S. Tetrahedron Lett. 1991, 32, 1125-1128.
31. 2O, pyridine).
32. 1H NMR. This result suggests that formation of 11 is taking place via both one-electron (by hydrogen atom abstraction, probably from solvent) and two-electron (by protonation of an organosamarium intermediate) processes. See, however, ref 3a.
33. 2 and that this binding affects the chemoselectivity of reductions of olefins by this reagent. Yacovan, A.; Hoz, S.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261-262.
34. 2 and that this binding affects the chemoselectivity of reductions of olefins by this reagent. Yacovan, A.; Hoz, S.; Bilkis, I. J. Am. Chem. Soc. 1996, 118, 261-262.
35. a = 10.7-12.1. Neta, P. Adv. Phys. Org. Chem. 1976, 12, 223-297. Molander has not observed any effect of proton sources on the diastereoselectivity of ketyl-olefin radical cyclizations in simple systems. Molander, G. A.; McKie J. Org. Chem. 1992, 57, 3132-3139.
36. a = 10.7-12.1. Neta, P. Adv. Phys. Org. Chem. 1976, 12, 223-297. Molander has not observed any effect of proton sources on the diastereoselectivity of ketyl-olefin radical cyclizations in simple systems. Molander, G. A.; McKie J. Org. Chem. 1992, 57, 3132-3139.
37. 2: Cronjé, J. J.; Holzapfel, C. W.; Williams, D. B. G. Tetrahedron Lett. 1996, 37, 1305.