Practical synthesis of a chiral ynamide: (R)-4-phenyl-3-(2-triisopropylsilylethynyl) oxazolidin-2-one [2-Oxazolidinone, 4-Phenyl-3-(2-triisopropylsilyl-ethynyl)-, (4R)-]

Organic Syntheses

Volumn 84, Issue , 2007, Pages 359-367

  Sagamanova, I K ^a   Kurtz, K C M ^a   Hsung, R P ^a   Marcantonio, Karen M ^a   Mathre, David J ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85026866955     PISSN: 00786209     EISSN: 16000730     Source Type: Book Series    
DOI: 10.15227/orgsyn.084.0359     Document Type: Article

References (59)

1. For reviews on ynamides, see: (a) Zificsak, C. A.; Mulder, J. A.; Hsung, R. P.; Rameshkumar, C.; Wei, L.-L. Tetrahedron 2001, 57, 7575.
2. (b) Zhang, Y.; Hsung, R. P. ChemTracts 2004, 17, 442.
3. (c) Katritzky, A. R.; Jiang, R.; Singh, S. K. Heterocycles 2004, 63, 1455.
4. For reviews on the synthesis of ynamides, see: (a) Tracey, M. R.; Hsung, R. P.; Antoline, J.; Kurtz, K. C. M.; Shen, L.; Slafer, B. W.; Zhang, Y., in Science of Synthesis, Houben-Weyl Methods of Molecular Transformations, Steve M. Weinreb, Ed. Georg Thieme Verlag KG: Chapter 21.4, 2005.
5. (b) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P. Synlett 2003, 1379.
6. For the first preparations of ynamides, see: Janousek, Z.; Collard, J.; Viehe, H. G. Angew. Chem., Int. Ed. 1972, 11, 917.
7. For some examples of alkynyl iodonium triflate salts, see: (a) Feldman, K. S.; Bruendl, M. M.; Schildknegt, K.; Bohnstedt, A. C. J. Org. Chem. 1996, 61, 5440.
8. (b) Witulski, B.; Stengel, T. Angew. Chem. Int. Ed. 1998, 37, 489.
9. (c) Witulski, B.; Stengel, T.; Fernàndez-Hernàndez, J. M. Chem. Commun. 2000, 1965.
10. (d) Witulski, B.; Buschmann, N.; Bergsträßer, U. Tetrahedron 2000, 56, 8473.
11. (e) Rainier, J. D.; Imbriglio, J. E. J. Org. Chem. 2000, 65, 7272.
12. (f) Brückner, D. Synlett 2000,1402.
13. (g) Fromont, C.; Masson, S. Tetrahedron 1999, 55, 5405.
14. For the synthesis of ynamides using copper catalyzed amidations, see: (a) Frederick, M. O.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P.; Huang, J.; Kurtz, K. C. M.; Shen, L.; Douglas, C. J. J. Am. Chem. Soc. 2003, 125, 2368.
15. (b) Zhang, Y.; Hsung R. P.; Tracey, M. R.; Kurtz, K. C. M.; Vera, E. L. Org. Lett. 2004, 6, 1151.
16. Also see: (a) Dunetz, J. R.; Danheiser, R. L. Org. Lett. 2003, 5, 4011.
17. (b) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727.
18. (c) Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
19. For the synthesis of ynamides using an based promoted elimination Zbeta-bromo enamides, see: Wei, L.-L.; Mulder, J. A.; Xiong, H.; Zificsak, C. A.; Douglas, C. J.; Hsung, R. P. Tetrahedron 2001, 57, 459.
20. Also see: Couty, S.; Barbazanges, M.; Meyer, C.; Cossy, J. Synlett 2005, 906.
21. For an impressive array of reports on the chemistry of ynamides just in the last three years, see: (a) For a special issue dedicated to the chemistry of ynamides, see: Tetrahedron-Symposium-In-Print: "Chemistry of Electron-Deficient Ynamines and Ynamides." Tetrahedron 2006, 62, Issue No.16.
22. (b) Tanaka, K.; Takeishi, K.; Noguchi, K. J. Am. Chem. Soc. 2006, 128, 4586.
23. (c) Couty, S.; Meyer, C.; Cossy, J. Angew. Chem. Int. Ed. 2006, 45, 6726.
24. (d) Dunetz, J. R.; Danheiser, R. L. J. Am. Chem. Soc. 2005, 127, 5776.
25. (e) Zhang, Y. Tetrahedron Lett. 2005, 46, 6483.
26. (f) Riddell, N.; Villeneuve, K.; Tam, W. Org. Lett. 2005, 7, 3681.
27. (g) Martinez-Esperon, M. F.; Rodriguez, D.; Castedo, L.; Saá, C. Org. Lett. 2005, 7, 2213.
28. (h) Bendikov, M.; Duong, H. M.; Bolanos, E.; Wudl, F. Org. Lett. 2005, 7, 783.
29. (i) Marion, F.; Coulomb, J.; Courillon, C.; Fensterbank, L.; Malacria, M. Org. Lett. 2004, 6, 1509.
30. (j) Rosillo, M.; Domínguez, G.; Casarrubios,L.; Amador, U.; Pérez-Castells, J. J. Org. Chem. 2004, 69, 2084.
31. (k) Couty, S.; Liégault, B.; Meyer, C.; Cossy, J. Org. Lett. 2004, 6, 2511.
32. (l) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 783.
33. (m) Rodríguez, D.; Castedo, L.; Saá, C. Synlett 2004, 377.
34. (n) Hirano, S.; Tanaka, R.; Urabe, H.; Sato, F. Org. Lett. 2004, 6, 727.
35. (o) Klein, M.; König, B. Tetrahedron 2004, 60, 1087.
36. (p) Marion, F.; Courillon, C.; Malacria, M. Org. Lett. 2003, 5, 5095.
37. (q) Witulski, B.; Alayrac, C.; Tevzaadze-Saeftel, L. Angew. Chem., Int. Ed. 2003, 42, 4257.
38. (r) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5, 67.
39. (s) Witulski, B.; Lumtscher, J.; Bergsträber, U. Synlett 2003, 708.
40. (t) Naud, S.; Cintrat, J.-C. Synthesis 2003, 1391.
41. (u) Witulski, B.; Alayrac, C. Angew. Chem. Int. Ed. 2002, 41, 3281.
42. (v) Saito, N.; Sato, Y.; Mori, M. Org. Lett. 2002, 4, 803.
43. (w) Timbart, J.-C.; Cintrat. J.-C. Chem. Eur. J. 2002, 8, 1637.
44. For our own recent applications of ynamides, see: (a) Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Chem. Commun. 2007, ASAP.
45. (b) Oppenheimer, J.; Johnson, W. L.; Tracey, M. R.; Hsung, R. P.; Yao, P.-Y.; Liu, R.; Zhao, K. Org. Lett. 2007, 9, ASAP.
46. (c) You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.; Lu, T.; Hsung, R. P. Synlett 2007, in press.
47. (d) Tracey, M. R.; Oppenheimer, J.; Hsung, R. P. J. Org. Chem. 2006, 71, 8629.
48. (e) Zhang, X.; Li, H.; You, L.; Tang, Y.; Hsung, R. P. Adv. Syn. Cat. 2006, 348, 2437.
49. (f) Zhang, X.; Hsung, R. P.; You, L. Organic Biomol. Chem. 2006, 6, 2679.
50. (g) Zhang, X.; Zhang, Y.; Huang, J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.; Sagamanova, I. K.; Tracey, M. R. J. Org. Chem. 2006, 71, 4170.
51. (h) Kurtz, K. C. M.; Frederick, M. O.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R.; Hsung, R. P. Tetrahedron 2006, 62, 3928.
52. (i) Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Organic Lett. 2006, 8, 231.
53. (j) Zhang, Y.; Hsung, R. P.; Zhang, X.; Huang, J.; Slafer, B. W.; Davis, A.; Org. Lett. 2005, 7, 1047.
54. (k) Tracey, M. R.; Zhang, Y.; Frederick, M. O.; Mulder, J. A.; Hsung, R. P. Org. Lett. 2004, 6, 2209.
55. (l) Shen, L.; Hsung, R. P. Tetrahedron Lett. 2003, 44, 9353.
56. (m) Frederick, M. O.; Hsung, R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5, 2663.
57. (n) Mulder, J. A.; Kurtz, K. C. M.; Hsung, R. P.; Coverdale, H. A.; Frederick, M. O.; Shen, L.; Zificsak, C. A. Org. Lett. 2003, 5, 1547.
58. (o) Huang, J.; Xiong, H.; Hsung, R. P.; Rameshkumar. C.; Mulder, J. A.; Grebe, T. P. Org. Lett. 2002, 4, 2417.
59. (p) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.; Zificsak, C. A. Org. Lett. 2002, 4, 1383.