Mild reductive opening of aryl pyranosides promoted by scandium(III) triflate

Journal of the American Chemical Society

Volumn 129, Issue 1, 2007, Pages 38-39

  Qin, Hua Li ^a   Lowe, Jason T ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRANOSIDE; SCANDIUM; TRIFLUOROMETHANESULFONIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; REDUCTION; RING OPENING;

CATALYSIS; GLYCOSIDES; MESYLATES; OXIDATION-REDUCTION; PYRANS; SCANDIUM; STEREOISOMERISM;

EID: 33846088470     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja067234o     Document Type: Article

References (31)

1. (a) Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W. L. Chem. Rev. 2002, 102, 2227.
2. (b) Longbottom, D. Synlett 1999, 2023 and references therein.
3. (c) Kobayashi, S. Eur. J. Org. Chem. 1999, 15.
4. (a) Sadow, A. D.; Tilley, T. D. J. Am. Chem. Soc. 2005, 127, 643.
5. (b) Rauniyar, V.; Hall, D. G. J. Am. Chem. Soc. 2004, 126, 4518.
6. (c) Sadow, A. D.; Tilley, T. D. J. Am. Chem. Soc. 2003, 125, 7971.
7. (d) Newitt, L. A.; Steel, P. G. J. Chem. Soc., Perkin Trans. 1 1997, 2033.
8. (e) Deguin, B.; Vogel, P.; Roulet, J. M. Tetrahedron Lett. 1997, 38, 6197.
9. (a) Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 3231.
10. (b) Lowe, J. T.; Panek, J. S. Org. Lett. 2005, 7, 1529.
11. (c) Su, Q.; Panek, J. S. J. Am. Chem. Soc. 2004, 126, 2425.
12. (d) Huang, H.; Panek, J. S. J. Am. Chem. Soc. 2000, 122, 9836.
13. (a) Nishikawa, T.; Koide, Y.; Kajii, S.; Wada, K.; Ishikawa, M.; Isobe, M. Org. Biomol. Chem. 2005, 3, 687.
14. (b) Umata, A.; Wakayama-shi, M. U.S. Patent 0,060,667, 2003.
15. (c) Baker, R. H.; Cornell, K. H.; Cron, M. J. J. Am. Chem. Soc. 1948, 70, 1490.
16. (a) Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 12288.
17. (b) Abell, A. D.; Massy-Westropp, R. A Tetrahedron 1985, 41, 2451.
18. (a) Gevorgyan, V.; Liu, J. X.; Rubin, M.; Benson, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 8919.
19. (b) DeNinno. M. P.; Etienne, J. B.; Duplantier, K. C. Tetrahedron Lett. 1995, 36, 669.
20. (a) Watanabe, S.; Sueyoshi, T.; Ichihara, M.; Uehara, C.; Iwamura, M. Org. Lett. 2001, 3, 255.
21. (b) For acyclic deoxygenation example using trialkyl silanes see: Sakai, N.; Hirasawa, M.; Konakahara, T. Tetrahedron Lett. 2005, 46, 6407.
22. 3, and trifluoroacetic acid. None provided acyclic materials. Triflie acid and TMSOTf provided acyclic material, albeit with lower yields.
23. 4/allylsilanes see: Oku, A; Homoto, Y: Harada, T. Chem. Lett. 1986, 1495.
24. (b) For allylation of benzylic alcohols/acetates see: Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705.
25. Stereochemistry of the benzylic center was determined through NOE measurements via the reduction of the azide of 3b and subsequent lactam formation (see Supporting Information for details).
26. (a) Jolly, C.; Morimoto, R. L. J. Natl. Cancer Inst. 2000, 92, 1564.
27. (b) Scheibel, T.; Buchner, J. Biochem. Pharmacol. 1998, 56, 675.
28. (a) Cheng, H.; Cao, X.; Xian, M.; Fang, L.; Cai, T. B.; Ji, J. J.; Tunae, J. B.; Sun, D.; Wang, P. G. J. Med. Chem. 2005, 48, 645.
29. (b) Andrus, M. B.; Meredith, E. L.; Hicken, E. J.; Simmons, B. L.; Glancey, R. R.; Ma, W. J. Org. Chem. 2003, 68, 8162.
30. Wrona, I. E.; Gabarda, A. E.; Evano, G.; Panek, J. S. J. Am. Chem. Soc. 2005, 127, 15026.
31. Andrus, M. B.; Meredith, E. L.; Sekhar, B. B. V. S. Org. Lett. 2001, 3, 259.