Acetal-vinyl sulfide cyclization on sugar substrates: Effect of structure and substituent

Journal of Organic Chemistry

Volumn 68, Issue 3, 2003, Pages 824-831

  Sasmal, Pradip K ^a   Maier, Martin E ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION;

CHEMICAL REACTIONS; ETHERS; KETONES; OLEFINS; ORGANIC ACIDS; SOLVENTS; VINYL RESINS;

SUGAR (SUCROSE);

ACETAL; ALKENE; BICYCLO COMPOUND; ETHER DERIVATIVE; GLUCOSIDE; KETONE; PYRANOSIDE; SUGAR; SULFIDE; TETRAHYDROFURAN DERIVATIVE; VINYL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

CATALYSIS; CYCLIZATION; ETHERS; FURANS; GLUCOSIDES; MODELS, MOLECULAR; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRANS; STEREOISOMERISM; VINYL CHLORIDE;

EID: 0037423170     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026163i     Document Type: Article

References (48)

1. MacMillan, D. W. C.; Overman, L. E.; Pennington, L. D. J. Am. Chem. Soc. 2001, 123, 9033-9044.
2. Bernardelli, P.; Moradei, O. M.; Friedrich, D.; Yang, J.; Gallou, F.; Dyck, B. P.; Doskotch, R. W.; Lange, T.; Paquette, L. A. J. Am. Chem. Soc. 2001, 123, 9021-9032.
3. Lindel, T. Angew. Chem. 1998, 110, 806-808; Angew. Chem., Int. Ed. 1998, 37, 774-776.
4. Lindel, T. Angew. Chem. 1998, 110, 806-808; Angew. Chem., Int. Ed. 1998, 37, 774-776.
5. Föhlisch, B.; Gehrlach, E.; Henle, G.; Boberlin, U.; Herter, R. J. Chem. Res., Synop. 1991, 136; J. Chem. Res., Miniprint 1991, 1462-1492.
6. Föhlisch, B.; Gehrlach, E.; Henle, G.; Boberlin, U.; Herter, R. J. Chem. Res., Synop. 1991, 136; J. Chem. Res., Miniprint 1991, 1462-1492.
7. Harmata, M.; Jones, D. E. J. Org. Chem. 1997, 62, 1578-1579.
8. Stark, C. B. W.; Pierau, S.; Wartchow, R.; Hoffmann, H. M. R. Chem.-Eur. J. 2000, 6, 684-691.
9. Sammes, P. G. Gazz. Chim. Ital. 1986, 116, 109-114.
10. Mascareñas, J. L.; Rumbo, A.; Castedo, L. J. Org. Chem. 1997, 62, 8620-8621.
11. Rodriguez, J. R.; Rumbo, A.; Castedo, L.; Mascareñas, J. L. J. Org. Chem. 1999, 64, 966-970.
12. Molander, G. A.; Cameron, K. O. J. Org. Chem. 1991, 56, 2617-2619.
13. Molander, G. A.; Eastwood, P. R. J. Org. Chem. 1995, 60, 4559-4565.
14. Alvarez, E.; Zurita, D.; Martín, J. D. Tetrahedron Lett. 1991, 32, 2245-2248.
15. Person, G.; Keller, M.; Prinzbach, H. Liebigs Ann. Chem. 1996, 507-527.
16. Sasmal, P. K.; Maier, M. E. Org. Lett. 2002, 4, 1271-1274.
17. Marson, C. M.; Campbell, J.; Hursthouse, M. B.; Malik, K. M. A. Angew. Chem. 1998, 110, 1170-1172.
18. Sonawane, H. R.; Maji, D. K.; Jana, G. H.; Pandey, G. J. Chem. Soc., Chem. Commun. 1998, 1773-1774.
19. Ohmura, H.; Smyth, G. D.; Mikami, K. J. Org. Chem. 1999, 64, 6056-6059.
20. López, F.; Castedo, L.; Mascarefias, J. L. J. Am. Chem. Soc. 2002, 124, 4218-4219.
21. Cho, Y. S.; Kim, H. Y.; Cha, J. H.; Pae, A. N.; Koh, H. Y.; Choi, J. H.; Chang, M. H. Org. Lett. 2002, 4, 2025-2028.
22. Castañeda, A.; Kucery, D. J.; Overman, L. E. J. Org. Chem. 1989, 54, 5695-5707.
23. Blumenkopf, T. A.; Bratz, M.; Castañeda, A.; Look, G. C.; Overman, L. E.; Rodriguez, D.; Thompson, A. S. J. Am. Chem. Soc. 1990, 112, 4386-4399.
24. Blumenkopf, T. A.; Look, G. C.; Overman, L. E. J. Am. Chem. Soc. 1990, 112, 4399-4403.
25. Bratz, M.; Bullock, W. H.; Overman, L. E.; Takemoto, T. J. Am. Chem. Soc. 1995, 117, 5958-5966.
26. Berger, D.; Overman, L. E.; Renhowe, P. A. J. Am. Chem. Soc. 1997, 119, 2446-2452.
27. Jaber, J. J.; Mitsui, K.; Rychnovsky, S. D. J. Org. Chem. 2001, 66, 4679-4686.
28. Magriotis, P. A.; Brown, J. T. Org. Synth. 1995, 72, 252-264.
29. Ugarkar, B. G.; DaRe, J. M.; Kopcho, J. J.; Brown, C. E., III; Schanzer, J. M.; Wiesner, J. B.; Erion, M. D. J. Med. Chem. 2000, 43, 2883-2893.
30. Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishikawa, M.; Satoh, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111,314-321.
31. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
32. Giuliano, R. M.; Villani, F. J., Jr. J. Org. Chem. 1995, 60, 202-211.
33. Crimmins, M. T.; Tabet, E. A. J. Am. Chem. Soc. 2000, 122, 5473-5476.
34. Liu, Z.; Classon, B.; Samuelsson, B. J. Org. Chem. 1990, 55, 4273-4275.
35. Stamatatos, L.; Sinay, P.; Pougny, J.-R. Tetrahedron 1984, 40, 1713-1719.
36. Still, W. C.; Barrish, J. C. J. Am. Chem. Soc. 1983, 105, 2487-2489.
37. Houk, K. N.; Rondan, N. G.; Wu, Y.-D.; Metz, J. T.; Paddón-Row, M. N. Tetrahedron 1984, 40, 2257-2274.
38. van Delft, F. L.; van der Marel, G. A.; van Boom, J. H. Synlett 1995, 1069-1070.
39. Hughes, I. W.; Overend, W. G.; Stacey, M. J. Chem. Soc. 1949, 2846-2849.
40. Rauter, A.; Figueiredo, J.; Ismael, M.; Canda, T.; Font, J.; Figueredo, M. Tetrahedron: Asymmetry 2001, 12, 1131-1146.
41. Petráková, E.; Kováč, P.; Glaudemans, C. P. J. Carbohydr. Res. 1992, 233, 101-112.
42. Overend, W. G.; Shafizadeh, F.; Stacey, M. J. Chem. Soc. 1950, 671-677.
43. Hung, S.-C.; Wong, C.-H. Angew. Chem. 1996, 108, 2829-2832; Angew. Chem., Int. Ed. Engl. 1996, 35, 2671-2674.
44. Hung, S.-C.; Wong, C.-H. Angew. Chem. 1996, 108, 2829-2832; Angew. Chem., Int. Ed. Engl. 1996, 35, 2671-2674.
45. Kim, K. S.; Szarek, W. A. Carbohydr. Res. 1982, 100, 169-176.
46. Olson, G.; Voss, M. E.; Hill, D. E.; Kahn, M.; Madison, V. S.; Cook, C. M. J. Am. Chem. Soc. 1990, 112, 323-333.
47. Hanna, I.; Ricard, L. Org. Lett. 2000, 2, 2651-2654.
48. Boyer, F.-D.; Hanna, I.; Nolan, S. P. J. Org. Chem. 2001, 66, 4094-4096.