Benzylsulfanyloxazolines in palladium-catalyzed cross-coupling reactions: A novel approach to chiral oxazolines

Synthesis

Volumn , Issue 6, 2007, Pages 0857-0864

  Leconte, Nicolas ^a   Pellegatti, Laurent ^a   Tatibouët, Arnaud ^a   Suzenet, Franck ^a   Rollin, Patrick ^a   Guillaumet, Gerald ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

Carbohydrates; Copper; Cross coupling; Palladium; Sulfur

Indexed keywords

BORON COMPOUNDS; CARBOHYDRATES; CATALYSTS; COPPER; PALLADIUM; REACTION KINETICS; SULFUR;

BENZYLSULFANYLOXAZOLINES; CHIRAL OXAZOLINES; CROSS COUPLING REACTIONS; ORGANOSTANNYL REAGENTS;

LIGANDS;

2 BENZYLSULFANYL 1,3 OXAZOLINE DERIVATIVE; 2 BENZYLSULFANYL 4,5 DIHYDRO(1',2' DIDEOXY BETA DEXTRO ARABINOFURANOSE) [1,2,D] OXAZOLE; BENZYLSULFANYLOXAZOLINE DERIVATIVE; BORON DERIVATIVE; CARBOHYDRATE; COPPER; OXAZOLINE DERIVATIVE; PALLADIUM; TIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; CROSS COUPLING REACTION; SYNTHESIS;

EID: 33947587524     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-965932     Document Type: Article

References (51)

1. For review, see: (a) Heck, R. F. Palladium Reagents in Organic Synthesis; Academic Press: New York, 1985.
2. (b) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley & Sons: New York, 1995.
3. (c) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508.
4. (d) Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457.
5. (e) Littke, A. F.; Fu, G. C. Angew. Chem. Int. Ed. 2002, 41, 4176.
6. (f) Dubbaka, S. R.; Vogel, P. Angew. Chem. Int. Ed. 2005, 44, 7674.
7. (a) Malleron, J.-L.; Fiaud, J.-C.; Legros, J.-Y. Handbook of Palladium-Catalysed Organic Reactions; Academic Press: London, 1997.
8. (b) Srogl, J.; Allred, G. D.; Liebeskind, L. S. J. Am. Chem. Soc. 1997, 119, 12376.
9. (c) Srogl, J.; Liu, W.; Marshall, D.; Liebeskind, L. S. J. Am. Chem. Soc. 1999, 121, 9449.
10. (d) Darses, S.; Genêt, J.-P.; Brayer, J.-L.; Demoute, J.-P. Tetrahedron Lett. 1997, 38, 4393.
11. (e) Kikukawa, K.; Kono, K.; Wada, F.; Matsuda, T. J. Org. Chem. 1983, 48, 1333.
12. (f) Pridgen, L. N. J. Org. Chem. 1981, 46, 5402.
13. (a) Liebeskind, L. S.; Srogl, J. J. Am. Chem. Soc. 2000, 122, 11260.
14. (b) Savarin, C.; Srogl, J.; Liebeskind, L. S. Org. Lett. 2001, 3, 91.
15. (c) Egi, M.; Liebeskind, L. S. Org. Lett. 2003, 5, 801.
16. (d) Kusturin, C. L.; Liebeskind, L. S.; Neumann, W. L. Org. Lett. 2002, 4, 983.
17. (e) Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Synlett 2002, 447.
18. (f) Liebeskind, L. S.; Srogl, J. Org. Lett. 2002, 4, 979.
19. (g) Alphonse, F.-A.; Suzenet, F.; Keromnes, A.; Lebret, B.; Guillaumet, G. Org. Lett. 2003, 5, 803.
20. (h) Richardson, C.; Rewcastle, G. W.; Hoyer, D.; Denny, W. A. J. Org. Chem. 2005, 70, 7436.
21. Velazquez, F.; Olivo, H. F. Curr. Org. Chem. 2002, 6, 1.
22. (a) Nagao, Y.; Yamada, S.; Kumagai, T.; Ochiai, M.; Fujita, E. J. Chem. Soc., Chem. Commun. 1985, 1418.
23. (b) Hsiao, C. N.; Liu, L.; Miller, M. J. J. Org. Chem. 1987, 52, 2201.
24. (c) Kazmierczak, F.; Helquist, P. J. Org. Chem. 1989, 54, 3988.
25. (d) Yan, T. H.; Lee, H. C.; Tan, C. W. Tetrahedron Lett. 1993, 34, 3559.
26. (e) Yan, T. H.; Tan, C. W.; Lee, H. C.; Huang, T. Y. J. Am. Chem. Soc. 1993, 115, 2613.
27. (f) Hsiao, C. N.; Liu, L.; Miller, M. J. J. Org. Chem. 1995, 60, 3301.
28. (g) Su, D. W.; Wang, Y. C.; Yan, T. H. Tetrahedron Lett. 1999, 40, 4197.
29. (h) Crimmins, M. T.; King, B. W.; Tabet, E. A.; Chaudhary, K. J. Org. Chem. 2001, 66, 894.
30. (i) Guz, N. R.; Phillips, A. J. Org. Lett. 2002, 4, 2253.
31. (j) Crimmins, M. T.; Katz, J. D.; Washburn, D. G.; Allwein, S. P.; McAtee, L. F. J. Am. Chem. Soc. 2002, 124, 5661.
32. (k) Meyers, A. I. J. Org. Chem. 2005, 70, 6137.
33. (a) Gueyrard, D.; Grumel, V.; Leoni, O.; Palmieri, S.; Rollin, P. Heterocycles 2000, 52, 827.
34. (b) Gueyrard, D.; Leoni, O.; Palmieri, S.; Rollin, P. Tetrahedron: Asymmetry 2001, 12, 337.
35. (c) Girniene, J.; Gueyrard, D.; Tatibouët, A.; Sackus, A.; Rollin, P. Tetrahedron Lett. 2001, 42, 2977.
36. (d) Girniene, J.; Tatibouët, A.; Sackus, A.; Yang, J.; Holman, G. D.; Rollin, P. Carbohydr. Res. 2003, 338, 711.
37. (e) Girniene, J.; Apremont, G.; Tatibouët, A.; Sackus, A.; Rollin, P. Tetrahedron 2004, 60, 2609.
38. (f) Pridgen, L. N.; Killmer, L. B. J. Org. Chem. 1981, 46, 5402.
39. (g) Pridgen, L. N.; Killmer, L. B.; Webb, R. L. J. Org. Chem. 1982, 47, 1985.
40. (h) Chenard, B. L. J. Org. Chem. 1983, 48, 2610.
41. 3d
42. (a) Desimoni, G.; Faita, G.; Jorgensen, K. A. Chem. Rev. 2006, 106, 3561.
43. (b) Corey, E. J.; Imai, N.; Zhang, H.-Y. J. Am. Chem. Soc. 1991, 113, 728.
44. (c) Ojima, I. Catalytic Asymmetric Synthesis; Wiley-VCH: New York, 2000.
45. (d) Hallman, K.; Macedo, E.; Nordström, K.; Moberg, C. Tetrahedron: Asymmetry 1999, 10, 4037; and references therein.
46. (e) Johnson, J. S.; Evans, D. A. Acc. Chem. Res. 2000, 33, 325.
47. (f) Ghosh, A. K.; Mathivanan, P.; Capiello, J. Tetrahedron: Asymmetry 1998, 9, 1.
48. (g) Imai, Y.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ikeda, I. Tetrahedron: Asymmetry 1996, 7, 2453.
49. Parlow, J. J.; Vazquez, M. L.; Flynn, D. L. Bioorg. Med. Chem. Lett. 1998, 8, 2391.
50. Peters, D.; Hörnfeldt, A.-B.; Gronowitz, S. J. Heterocycl. Chem. 1990, 27, 2165.
51. Fülöp, F.; Csirinyi, G.; Bernath, G. Synthesis 1985, 1149.