Stereoselective C-glycoside formation by a rhodium(I)-catalyzed 1,4-addition of arylboronic acids to acetylated enones derived from glycals

Organic Letters

Volumn 3, Issue 16, 2001, Pages 2571-2573

  Ramnauth, Jailall ^a   Poulin, Odile ^a   Bratovanov, Svetoslav S ^a   Rakhit, Suman ^a   Maddaford, Shawn P ^a  

^a YORK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCOSIDE; RHODIUM;

ACETYLATION; ARTICLE; CATALYSIS; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOISOMERISM; SYNTHESIS;

ACETYLATION; BORONIC ACIDS; CATALYSIS; GLYCOSIDES; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; RHODIUM; STEREOISOMERISM;

EID: 0035833738     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016245d     Document Type: Article

References (19)

1. (a) Jarmillo, C.; Knapp, S. Synthesis 1994, 1.
2. (b) Postema, M. H. D. Tetrahedron 1992, 48, 8545.
3. Hacksell, C. V.; Daves, G. D., Jr. J. Med. Chem. 1985, 22, 1.
4. (a) Townsend, L. B.; Devivar, R. V.; Turk, S. R.; Nassiri, M. R.; Drach, J. C. J. Med. Chem. 1995, 38, 4098.
5. (b) Gudmunsson, K. S.; Drach, J. C.; Townsend, L. B. J. Org. Chem. 1997, 62, 3453.
6. Du, Y.; Linhardt, R. J.; Vlahov, I. R. Tetrahedron 1998, 54, 9913 and references therein.
7. Moineau, C.; Bolitt, V.; Sinou, D. J. Chem. Soc., Chem. Commun. 1995, 1103.
8. Benhaddou, R.; Czernecki, S.; Ville, G. J. Org. Chem. 1992, 57, 4612.
9. (a) Sakai, M.; Hayashi, H.; Miyaura, N. Organometallics 1997, 16, 4229.
10. (b) Takaya, Y.; Ogasawara, M.; Hayashi, T. J. Am. Chem. Soc. 1998, 120, 5579.
11. (c) Sakuma, S.; Sakai, M.; Itooka, R.; Miyaura, N. J. Org. Chem. 2000, 65, 5951.
12. Kirschning, A.; Drager, G.; Harders, J. Synlett 1993, 289.
13. Brakta, M.; Farr, R. N.; Chaguir, B.; Massiot, G.; Lavaud, C.; Anderson, W. R., Jr.; Sinou, D.; Daves, G. D., Jr. J. Org. Chem. 1993, 58, 2992.
14. 2O, and 1.0 mL of dioxane was heated at reflux for 4 h. After this time, the reaction mixture was diluted with ethyl acetate (10 mL) and filterd through a pad of silica gel. The filtrate was concentrated and subjected to silica gel flash column chromatography using 80% hexanes/20% ethyl actetate as eluant.
15. Greico, P. A.; Speake, J. D. Tetrahedron Lett. 1998, 39, 1275.
16. Wright, S. W.; Hageman, D. L.; McClure, L. D. J. Org. Chem. 1994, 59, 6095.
17. Suzuki, A. Acc. Chem. Res. 1982, 15, 178.
18. Fürstner, A.; Krause, H. Adv. Synth. Catal. 2001, 4, 343.
19. Oi, S.; Mono, M.; Inoue, Y. J. Chem. Soc., Chem. Commun. 1997, 1621.