Palladium-catalyzed reactions of acetoxyenynes with triorganoindium reagents

Tetrahedron Letters

Volumn 47, Issue 50, 2006, Pages 8905-8910

  Metza Jr , John T ^a   Terzian, Raffi A ^a   Minehan, Thomas ^a  

^a CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

INDIUM; PALLADIUM; REAGENT; TRIORGANOINDIUM; UNCLASSIFIED DRUG;

ARTICLE; ATOM; CATALYSIS; CHEMICAL REACTION; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE; STEREOISOMERISM;

EID: 33750633342     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.10.043     Document Type: Article

References (59)

1. For reviews on the chemistry of indium, see:. Chan T.H., Li C.J., Lee M.C., and Wei Z.Y. Can. J. Chem. 72 (1994) 1181
2. Li C.J. Chem. Rev. 93 (1993) 2023
3. Cintas P. Synlett (1995) 1087
4. Li C.J. Tetrahedron 52 (1996) 5643
5. Li C.J., and Chan T.H. Organic Reactions in Aqueous Media (1997), Wiley, New York
6. In: Grieco P.A. (Ed). Organic Synthesis in Water (1998), Thomson Science, Glasgow, Scotland
7. Li C.J., and Chan T.H. Tetrahedron 55 (1999) 11149
8. Li C.J. Chem. Rev. 105 (2005) 3095
9. Perez I., Sestelo J.P., and Sarandeses L.A. Org. Lett. 1 (1999) 1267
10. Perez I., Sestelo J.P., and Sarandeses L.A. J. Am. Chem. Soc. 123 (2001) 4155
11. Pena M.A., Perez I., Perez Sestelo J., and Sarandeses L.A. Chem. Commun. 19 (2002) 2246
12. Nomura R., Miyazaki S., and Matsuda H. J. Am. Chem. Soc. 114 (1992) 2738
13. Takami K., Yorimitsu H., Shinokubo H., Matsubara S., and Oshima K. Org. Lett. 3 (2001) 1997
14. Lee P.H., Sung S., and Lee K. Org. Lett. 3 (2001) 3201
15. Lee P.H., Lee S.W., and Saemoon D. Org. Lett. 5 (2003) 4963
16. Lehmann U., Awasthi S., and Minehan T. Org. Lett. 5 (2003) 2405
17. Pena M.A., Sestelo J.P., and Sarandeses L.A. Synthesis 3 (2005) 485
18. Rodriguez D., Sestelo J.P., and Sarandeses L.A. J. Org. Chem. 68 (2003) 2518
19. Baker L.A., and Minehan T.G. J. Org. Chem. 69 (2004) 3957
20. Rodriguez D., Perez Sestelo J., and Sarandeses L.A. J. Org. Chem. 69 (2004) 8136
21. Riveiros R., Rodriguez D., Perez Sestelo J., and Sarandeses L.A. Org. Lett. 8 (2006) 1403
22. Goeta A., Salter M.M., and Shah H. Tetrahedron 62 (2006) 3582
23. Lee P.H., Kim S., Lee K., Seomoon D., Kim H., Lee S., Kim M., Han M., Noh K., and Livinghouse T. Org. Lett. 6 (2004) 4825
24. Kang S.-K., Lee S.-W., Jung J., and Lim Y. J. Org. Chem. 67 (2002) 4376
25. Salter M.M., and Sardo-Inffiri S. Synlett (2002) 2068
26. Yanada R., Nishimori N., Matsumura A., Fujii N., and Takemoto Y. Tetrahedron Lett. 43 (2002) 4585
27. Kang H.-Y., Kim Y.-T., Yu Y.-K., Cha J.W., Cho Y.S., and Koh H.Y. Synlett (2004) 45
28. Nair V., Ros S., Jayan C.C., and Pillai B.S. Tetrahedron 60 (2004) 1959
29. Takami K., Yorimitsu H., and Oshima K. Org. Lett. 4 (2002) 2993
30. Price S., Edwards S., Wu T., and Minehan T.G. Tetrahedron Lett. 45 (2004) 5197
31. Ihle N.C., and Heathcock C.H. J. Org. Chem. 58 (1993) 560
32. 2O, pyridine) of the corresponding allylic alcohol:. Marshall J.A., Piettre A., Paige M.A., and Valeriote F. J. Org. Chem. 68 (2003) 1771
33. 2O, pyridine) of the corresponding allylic alcohol:. Trost B.M., and Lee D.C. J. Org. Chem. 54 (1989) 2271
34. For a discussion of the Thorpe-Ingold effect, see:. Beesley R.M., Ingold C.K., and Thorpe J.F. J. Chem. Soc. 107 (1915) 1080
35. Bruice T.C., and Pandit U.K. J. Am. Chem. Soc. 82 (1960) 5858
36. Jung M.E., and Gervay J. J. Am. Chem. Soc. 113 (1991) 224
37. Jung M.E., and Kiankarimi M. J. Org. Chem. 63 (1998) 2968
38. Cui D.-M., Tsuzuki T., Miyake K., Ikeda S., and Sato Y. Tetrahedron 54 (1998) 1063
39. 3In; see Ref. 3d.
40. Oppolzer W., and Ruiz-Montes J. Helv. Chim. Acta 76 (1993) 1266
41. A similar result was obtained when tris(phenylethynyl)indium was employed in an attempted palladium-catalyzed allylic substitution of cyclohex-2-enyl acetate: see Ref. 3b.
42. Miura T., Shimada M., and Murakami M. J. Am. Chem. Soc. 127 (2005) 1094
43. Zhang Q., Xu W., and Lu X. J. Org. Chem. 70 (2005) 1505
44. 2O, pyridine) of the corresponding allylic alcohol:. Kressierer C.J., and Mueller T.J. Org. Lett. 7 (2005) 2237
45. 3-catalyzed atom-transfer cyclization of enynes:. Cook G.R., and Hiyashi R. Org. Lett. 8 (2006) 1045
46. A similar observation has been noted by Sarandeses in his studies of organoindium-mediated substitution reactions of allylic and propargylic halides and esters; see Refs. 3c and 3d.
47. Beachley O.T., MacRae D.J., Kovalevsky A.Y., Zhang Y., and Li X. Organometallics 21 (2002) 4632
48. Beachley O.T., MacRae D.J., Churchill M.R., Kovalevsky A.Y., and Robirds E.S. Organometallics 22 (2003) 3991
49. Beachley O.T., MacRae D.J., Churchill M.R., Kovalevsky A.Y., and Robirds E.S. Organometallics 22 (2003) 5152
50. The sodium methoxide used in the preparation of the aryldimethoxyindium solutions was generated by adding 2 M equiv (relative to indium trichloride) of sodium metal to sufficient methanol to make a 10 M solution; this 10 M methanolic solution was then quantitatively transferred to the THF solution of arylindiumdichloride.
51. 2 in solution.
52. 2O, pyridine) of the corresponding allylic alcohol:. Baldwin J.E., Chesworth R., Parker J.S., and Russell A.T. Tetrahedron Lett. 36 (1995) 9551
53. 2O, pyridine) of the corresponding allylic alcohol:. Lee H.-Y., Kim H.Y., Tae H., Kim B.G., and Lee J. Org. Lett. 5 (2003) 3439
54. 2O, pyridine).
55. 2O, pyridine) furnished 7c.
56. 2O, pyridine) furnished 7e.
57. 2O, pyridine) furnished 7f.
58. For a discussion of the mechanism of a related palladium-catalyzed zinc-ene reaction, see:. Oppolzer W., and Schroder F. Tetrahedron Lett. 35 (1994) 7939
59. 2O in hexanes) affords the substitution products.