Novel intramolecular allylindination of terminal alkynes in aqueous media

Synlett

Volumn , Issue 12, 2002, Pages 2068-2070

  Salter, Matthew M ^a   Sardo Inffiri, Sofia ^a  

^a KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

Aqueous; Cyclisation; Enyne; Indium; Intramolecular

Indexed keywords

ALKYNE DERIVATIVE; ALLYL COMPOUND; BROMINE DERIVATIVE; HETEROCYCLIC COMPOUND;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION;

EID: 0036454162     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35571     Document Type: Article

References (51)

1. For recent reviews on the subject of organoindium chemistry see: (a) Cintas, P. Synlett 1995, 1087. (b) Li, C.-J. Tetrahedron 1996, 52, 5643. (c) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149. (d) Chauhan, K. K.; Frost, C. G. J. Chem. Soc. Perkin Trans. 1 2000, 3015.
2. For recent reviews on the subject of organoindium chemistry see: (a) Cintas, P. Synlett 1995, 1087. (b) Li, C.-J. Tetrahedron 1996, 52, 5643. (c) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149. (d) Chauhan, K. K.; Frost, C. G. J. Chem. Soc. Perkin Trans. 1 2000, 3015.
3. For recent reviews on the subject of organoindium chemistry see: (a) Cintas, P. Synlett 1995, 1087. (b) Li, C.-J. Tetrahedron 1996, 52, 5643. (c) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149. (d) Chauhan, K. K.; Frost, C. G. J. Chem. Soc. Perkin Trans. 1 2000, 3015.
4. For recent reviews on the subject of organoindium chemistry see: (a) Cintas, P. Synlett 1995, 1087. (b) Li, C.-J. Tetrahedron 1996, 52, 5643. (c) Li, C.-J.; Chan, T.-H. Tetrahedron 1999, 55, 11149. (d) Chauhan, K. K.; Frost, C. G. J. Chem. Soc. Perkin Trans. 1 2000, 3015.
5. (a) With aldehydes: Lombardo, M.; Girotti, R.; Morganti, S.; Trombini, C. Org. Lett. 2001, 3, 2981.
6. (b) With ketones: Alcaide, B.; Almendros, P.; Rodriguez-Acebes, R. J. Org. Chem. 2002, 67, 1925.
7. (c) With imines: Vilaivan, T.; Winotapan, C.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2001, 42, 9073.
8. (d) Beuchet, P.; Marrec, M. L.; Mosset, P. Tetrahedron Lett. 1992, 33, 5959.
9. (e) With sulfonimines: Lu, W.; Chan, T. H. J. Org. Chem. 2001, 66, 3467.
10. (f) With acyl cyanides: Yoo, B.-W.; Lee, S.-J.; Choi, K.-H.; Keum, S.-R.; Ko, J.-J.; Choi, K.-I.; Kim, J.-H. Tetrahedron Lett. 2001, 42, 7287.
11. (g) With acetals: Kwon, J. S.; Pae, A. N.; Choi, K. I.; Koh, H. Y.; Kim, Y.; Cho, Y. S. Tetrahedron Lett. 2001, 42, 1957.
12. (h) With epoxides: Yadav, J. S.; Anjaneyulu, S.; Ahmed, M. M.; Subba Reddy, B. V. Tetrahedron Lett. 2001, 42, 2557; and references therein.
13. (a) Chappell, M. D.; Halcomb, R. L. Org. Lett. 2000, 2, 2003.
14. (b) Hirashita, T.; Kinoshita, K.; Yamamura, H.; Kawai, M.; Araki, S. J. Chem. Soc., Perkin Trans. 1 2000, 825.
15. (a) Araki, S.; Horie, T.; Kato, M.; Hirashita, T.; Yamamura, H.; Kawai, M. Tetrahedron Lett. 1999, 40, 2331.
16. (b) Lee, P. H.; Ahn, H.; Lee, K.; Sung, S.-Y.; Kim, S. Tetrahedron Lett. 2001, 42, 37.
17. (a) Yadav, J. S.; Subba Reddy, B. V.; Muralidhar Reddy, M. Tetrahedron Lett. 2000, 41, 2663.
18. (b) Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 2001, 955.
19. (c) Ranu, B. C.; Samanta, S.; Guchhait, S. K. J. Org. Chem. 2001, 66, 4102.
20. (d) Ranu, B. C.; Dutta, J.; Guchhait, S. K. Org. Lett. 2001, 3, 2603.
21. (a) Araki, S.; Kamei, T.; Hirashita, T.; Yamamura, H.; Kawai, M. Org. Lett. 2000, 2, 847.
22. (b) Pérez, I.; Sestelo, J. P.; Sarandeses, L. A. J. Am. Chem. Soc. 2000, 122, 4153.
23. (c) Takami, K.; Yorimitsu, H.; Shinokubo, H.; Matsubara, S.; Oshima, K. Org. Lett. 2001, 3, 1997.
24. (d) Hirashita, T.; Yamamura, H.; Kawai, M.; Araki, S. Chem. Commun. 2001, 387.
25. (e) Cooper, I. R.; Grigg, R.; MacLachlan, W. S.; Thornton-Pett, M.; Sridharan, V. Chem. Commun. 2002, 1372.
26. Araki, S.; Imai, A.; Shimizu, K.; Yamada, M.; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841.
27. Araki, S.; Usui, H.; Kato, M.; Butsugan, Y. J. Am. Chem. Soc. 1996, 118, 4699.
28. (a) Ranu, B. C.; Majee, A. Chem. Commun. 1997, 1225.
29. (b) Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1997, 62, 2318.
30. (c) Klaps, E.; Schmid, W. J. Org. Chem. 1999, 64, 7537.
31. Fujiwara, N.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4095.
32. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
33. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
34. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
35. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
36. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
37. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
38. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
39. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
40. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
41. For some examples of alternative transition metal-mediated enyne cycloisomerisation reactions see: (a) With Cr: Nishikawa, T.; Kakiya, H.; Shinokubo, H.; Oshima, K. J. Am. Chem. Soc. 2001, 123, 4629. (b) With Cu: Ajamian, A.; Gleason, J. L. Org. Lett. 2001, 3, 4161. (c) With Ni: Tsuzuki, T.; Miyake, K.; Ikeda, S.-I.; Sato, Y. Tetrahedron 1998, 54, 1063. (d) With Pd: Nishida, M.; Adachi, N.; Onozuna, K.; Matsumura, H.; Mori, M. J. Org. Chem. 1998, 63, 9158. (e) With Pt: Méndez, M.; Muñoz, M. P.; Nevado, C.; Cárdenas, D. J.; Echavarren, A. M. J. Am. Chem. Soc. 2001, 123, 10511. (f) With Rh: Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2001, 123, 4609. (g) With Ru: Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2002, 124, 4178. (h) With Sn: Fernández-Rivas, C.; Méndez, M.; Echavarren, A. M. J. Am. Chem. Soc. 2000, 122, 1221. (i) With Ti: Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 7026. (j) With Zr: Gordon, G. J.; Luker, T.; Tuckett, M. W.; Whitby, R. J. Tetrahedron 2000, 56, 2113; and references therein.
42. Marshall, J. A.; Grant, C. M. J. Org. Chem. 1999, 64, 8214.
43. (a) Canac, Y.; Levoirier, E.; Lubineau, A. J. Org. Chem. 2001, 66, 3206.
44. (b) Shin, J. A.; Cha, J. H.; Pae, A. N.; Choi, K. I.; Koh, H. Y.; Kang, H.-Y.; Cho, Y. S. Tetrahedron Lett. 2001, 42, 5489.
45. (a) Loh, T.-P.; Tan, K.-T.; Yang, J.-Y.; Xiang, C.L. Tetrahedron Lett. 2001, 42, 8701.
46. (b) Loh, T.-P.; Tan, K.-T.; Hu, Q.-Y. Tetrahedron Lett. 2001, 42, 8705.
47. For a general introduction to the use of water as a solvent for organic synthesis see: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Media; Klewer Academic Publishers: Dordrect, 1997. (c) Organic Synthesis in Water; Greico, P. A., Ed.; Blackie Academic & Professional: London, 1998.
48. For a general introduction to the use of water as a solvent for organic synthesis see: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Media; Klewer Academic Publishers: Dordrect, 1997. (c) Organic Synthesis in Water; Greico, P. A., Ed.; Blackie Academic & Professional: London, 1998.
49. For a general introduction to the use of water as a solvent for organic synthesis see: (a) Li, C.-J. Chem. Rev. 1993, 93, 2023. (b) Li, C.-J.; Chan, T. H. Organic Reactions in Aqueous Media; Klewer Academic Publishers: Dordrect, 1997. (c) Organic Synthesis in Water; Greico, P. A., Ed.; Blackie Academic & Professional: London, 1998.
50. +], 193 (36.5), 165 (65.1), 154 (74.3), 137 (68.1), 136 (61.7), 105 (100), 91 (49.7), 77 (49.1).
51. 13C, IR and MS data consistent with the structures reported.