Sulfenic acids in the carbohydrate field. Synthesis of transient glycosulfenic acids and their addition to unsaturated acceptors

Journal of Organic Chemistry

Volumn 67, Issue 20, 2002, Pages 6925-6930

  Aucagne, Vincent ^a   Aversa, Maria C ^b   Barattucci, Anna ^b   Bonaccorsi, Paola ^b   Giannetto, Placido ^b   Rollin, Patrick ^a   Tatibouët, Arnaud ^a  

^a UNIVERSITY OF MESSINA   (Italy)

^b Université d'Orléans   (France)

Author keywords

[No Author keywords available]

Indexed keywords

UNSATURATED ACCEPTORS;

ADDITION REACTIONS; ORGANIC ACIDS; SUGAR (SUCROSE);

SYNTHESIS (CHEMICAL);

CARBOHYDRATE; GLYCOSULFENIC ACID DERIVATIVE; SULFENIC ACID DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; STEREOSPECIFICITY; SYNTHESIS;

CHROMATOGRAPHY, THIN LAYER; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; GLYCOSIDES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFENIC ACIDS; TEMPERATURE;

EID: 0037019972     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025938k     Document Type: Article

References (26)

1. Driguez, H. Top. Curr. Chem. 1997, 187, 85-116.
2. Knapp, S.; Malolanarasimhan, K. Org. Lett. 1999, 1, 611-613 and references therein.
3. Ibatullin, F. M.; Selivanov, S. I.; Shavva A. G. Synthesis 2001, 3, 419-422.
4. Ibatullin, F. M.; Shabalin, K. A.; Jänis, J. V.; Selivanov, S. I. Tetrahedron Lett. 2001, 42, 4565-4567.
5. Garuti, L.; Roberti, M.; Giovanninetti, G.; Gaggi, R.; Defaye, J.; Driguez, H. Pharm. Acta Helv. 1988, 63, 202-205.
6. Davis, B. G. J. Chem. Soc., Perkin Trans. 1 2000, 2137-2160 and references therein.
7. Kahne, D.; Walker, S.; Cheng, Y.; Van Engen, D. J. Am. Chem. Soc. 1989, 111, 6881-6882.
8. Gildersleeve, J.; Pascal, R. A., Jr.; Kahne, D. J. Am. Chem. Soc. 1998, 120, 5961-5969.
9. Thompson, C.; Ge, M.; Kahne, D. J. Am. Chem. Soc. 1999, 121, 1237-1244.
10. Garegg, P. J. Adv. Carbohydr. Chem. 1997, 52, 179-205.
11. Kakarla, R.; Dulina, R. G.; Hatzenbuhler, N. T.; Hui, Y. W.; Sofia, M. J. J. Org. Chem. 1996, 61, 8347-8349.
12. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Policicchio, M. J. Org. Chem. 2001, 66, 4845-4851.
13. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Jones, D. N. J. Org. Chem. 1997, 62, 4376-4384.
14. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Nicolò, F. J. Org. Chem. 1999, 64, 2114-2118.
15. Cerny, M.; Pacák, J. Collect. Czech. Chem. Commun. 1959, 24, 2566-2569.
16. Khiar, N. Tetrahedron Lett. 2000, 41, 9059-9063.
17. Udodong, U. E.; Fraser-Reid, B. J. Org. Chem. 1989, 54, 2103-2112.
18. McCarter, J. D.; Adam, M. J.; Braun, C.; Namchuk, M.; Tull, D.; Withers, S. G. Carbohydrate Res. 1993, 249, 77-90.
19. Smith, M. B.; March, J. March's Advanced Organic Chemistry. Reactions, Mechanisms, and Structure, 5th ed.; John Wiley & Sons: New York, 2001; pp 1322-1336.
20. Cubbage, J. W.; Guo, Y.; McCulla, R. D.; Jenks, W. S. J Org. Chem. 2001, 66, 8722-8736.
21. Blanc-Muesser, M.; Driguez, H.; Joseph, B.; Viaud, M. C.; Rollin, P. Tetrahedron Lett. 1990, 31, 3867-3868.
22. Crich, D.; Mataka, J.; Sun, S.; Lam, K. C.; Rheingold, A. L.; Wink, D. J. Chem. Commun. 1998, 2763-2764.
23. Alonso, I.; Carretero, J. C.; García Ruano, J. L. J. Org. Chem. 1994, 59, 1499-1508.
24. Liu, J.; Huang, C.-Y.; Wong, C.-H. Tetrahedron Lett. 2002, 43, 3447-3448.
25. Kucherov, V. F.; Grigor'eva, N. Ya.; Zemskova, I. I. Zh. Obshchei Khim. 1961, 31, 457-469
26. (Chem. Abstr. 1961, 55, 22174a).