Suzuki-Miyaura cross-coupling of α-phosphoryloxy enol ethers with arylboronic acids

Tetrahedron Letters

Volumn 49, Issue 26, 2008, Pages 4142-4144

  Pedzisa, Lee ^a   Vaughn, Ian W ^a   Pongdee, Rongson ^a  

^a Department of Chemistry and Biochemistry   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; BORONIC ACID DERIVATIVE; ETHER DERIVATIVE; PYRAN DERIVATIVE;

ARTICLE; CROSS COUPLING REACTION; SUZUKI MIYAURA CROSS COUPLING;

EID: 43849091460     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.04.116     Document Type: Article

References (42)

1. For a recent review on the application of palladium-catalyzed reactions in the total synthesis of natural products see:. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4442
2. Tsushima K., Araki K., and Murai A. Chem. Lett. (1989) 1313-1316
3. Tsushima K., and Murai A. Chem. Lett. (1990) 761-764
4. Barber C., Jarowicki K., and Kocienski P. Synlett (1991) 197-198
5. Tsushima K., and Murai A. Tetrahedron Lett. 33 (1992) 4345-4348
6. Nicolaou K.C., Theodorakis E.A., Rutjes F.P.J.T., Tiebes J., Sato M., Unterstellar E., and Xiao X.-Y. J. Am. Chem. Soc. 117 (1995) 1171-1172
7. Nicolaou K.C., Rutjes F.P.J.T., Theodorakis E.A., Tiebes J., Sato M., and Unterstellar E. J. Am. Chem. Soc. 117 (1995) 1173-1174
8. Fujiwara K., Tsunashuma M., Awakura D., and Murai A. Tetrahedron Lett. 36 (1995) 8263-8266
9. Nicolaou K.C., Sato M., Miller N.D., Gunzner J.L., Renaud J., and Unterstellar E. Angew. Chem., Int. Ed. 35 (1996) 889-891
10. Nicolaou K.C., Shi G.-Q., Gunzner J.L., Gärtner P., and Yang Z. J. Am. Chem. Soc. 119 (1997) 5467
11. Nan Y., and Yang Z. Tetrahedron Lett. 40 (1999) 3321
12. Huffman M.A., and Yasuda N. Synlett (1999) 471
13. Lepifre F., Buon C., Rabot R., Bouyssou P., and Coudert G. Tetrahedron Lett. 40 (1999) 6373
14. Nicolaou K.C., Wallace P.A., Shi S., Ouellette M.A., Bunnage M.E., Gunzner J.L., Agrios K.A., Shi G.-Q., Gärtner P., and Yang Z. Chem. Eur. J. 5 (1999) 618
15. Sasaki M., Fuwa H., Ishikawa M., and Tachibana K. Org. Lett. 1 (1999) 1075
16. Lepifre F., Clavier S., Bouyssou P., and Coudert G. Tetrahedron 57 (2001) 6969
17. Sasaki M., Ishikawa M., Fuwa H., and Tachibana K. Tetrahedron 58 (2002) 1889
18. Occhiato E.G., Prandi C., Ferrali A., Guarna A., and Venturello P. J. Org. Chem. 68 (2003) 9728
19. Sasaki M., and Fuwa H. Synlett (2004) 1851
20. Larsen U.S., Martiny L., and Begtrup M. Tetrahedron Lett. 46 (2005) 4261
21. Fuwa H., and Sasaki M. Org. Lett. 9 (2007) 3347
22. Sasaki M., and Tachibana K. Tetrahedron Lett. 48 (2007) 3181
23. Sasaki M. Bull. Chem. Soc. Jpn. 80 (2007) 856
24. Anderson D.M. Sci. Am. 271 (1994) 62
25. Anderson D.M. Nature (London) 388 (1997) 513
26. Baker R. And The World Turned To Blood (1997), Simon and Schuster, New York
27. Benhaddou R., Czernecki S., and Ville G. J. Org. Chem. 57 (1992) 4612
28. Boyd V.A., Drake B.E., and Sulikowski G.A. J. Org. Chem. 58 (1993) 3191
29. Friesen R.W., Loo R.W., and Sturino C.F. Can. J. Chem. 72 (1994) 1262
30. Hosoya T., Takashiro E., Matsumoto T., and Suzuki K. J. Am. Chem. Soc. 116 (1994) 1004
31. Parker K.A., and Koh Y.-h. J. Am. Chem. Soc. 116 (1994) 11149
32. Toshima K., Matsuo G., Ishizuka T., Ushiko Y., Nakata M., and Matsumura S. J. Org. Chem. 63 (1998) 2307
33. Pulley S.R., and Carey J.P. J. Org. Chem. 63 (1998) 5275
34. Du Y., and Linhardt R.J. Tetrahedron 54 (1998) 9913
35. Calimente D., and Postema M.H.D. J. Org. Chem. 64 (1999) 1770
36. Kaelin Jr. D.E., Lopez O.D., and Martin S.F. J. Am. Chem. Soc. 123 (2001) 6937
37. Kaelin Jr. D.E., Sparks S.M., Plake H.R., and Martin S.F. J. Am. Chem. Soc. 125 (2003) 12994
38. Lehmann U., Awasthi S., and Minehan T. Org. Lett. 5 (2003) 2405
39. Li H., Procko K., and Martin S.F. Tetrahedron Lett. 47 (2006) 3485
40. Denmark S.E., and Neuville L. Org. Lett. 2 (2000) 3221
41. The Suzuki-Miyaura cross-coupling reaction of enol phosphates has been reported in modest to poor yields. See: Refs. 3b and 3k.
42. 2NEt) was found to suppress the protodestannylation of a vinylstannane involved in a Stille cross-coupling reaction:. Smith III A.B., and Ott G.R. J. Am. Chem. Soc. 120 (1998) 3935