Regio- and stereoselectivity in stannyl- and silylcupration of alkynes and enynes using proton sources

Synlett

Volumn , Issue 10, 1998, Pages 1129-1131

  Betzer, Jean François ^a   Pancrazi, Ange ^a  

^a LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001059063     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1864     Document Type: Article

References (42)

1. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis: Butterworths: London 1987.
2. For stannylcupration of enynes see: Oehlschlager, A. C. Tetrahedron 1991, 47, 1163.
3. Yokokawa, F.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1993, 34, 6559.
4. Barbero, A.; Cuadrado, P.; Fleming, I.; Gonzalez, A. M; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1992, 351.
5. For carbometallation of enynes see: Uenishi, J.-I.; Kawahama, R.; Tanio, A.; Wakabayashi, S. J. Chem. Soc., Chem. Commun. 1993, 1438.
6. For stannylmetallation of alkynes see: Hibino, J.-I.; Matsubara, S.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 2151.
7. Barbero, A.; Cuadrado, P.; Fleming, I.; Gonzales, A. M.; Pulido, F. J.; Rubio, R. J. Chem. Soc., Perkin Trans I 1993, 1657.
8. Beaudet, I.; Launay, V.; Parrain, J.-L.; Quintard, J.-P. Tetrahedron Lett. 1995, 36, 389.
9. Zhang, H. X.; Guibé, F.; Balavoine, G. J. Org. Chem. 1990, 55, 1857.
10. Trost, B. M.; Li, C.-J. Synthesis 1994, 1267.
11. Ichinose, Y.; Oda, H.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3468.
12. Kikukawa, K.; Umekawa, H.; Wada, F.; Matsuda, T. Chem. Lett. 1988, 881.
13. Zhang, H. X.; Cochran, J. C.; Bronk, B. S.; Terrence, K. M.; Phillips, H. K. Tetrahedron Lett. 1990, 31, 6621.
14. Rossi, R.; Carpita, A.; Cossi, P. Synth. Commun. 1993, 23, 143.
15. For trans hydrostannylation of alkynes, see also: Asao, N.; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1995, 2405.
16. For silastannylation see: Hada, M.; Tanaka, Y.; Ito, M.; Murakami, M.; Amii, H.; Ito, Y.; Nakatsuji, H. J. Am. Chem. Soc. 1994, 116, 8754.
17. Betzer, J.-F.; Ardisson, J.; Lallemand, J.-Y.; Pancrazi, A. Tetrahedron Lett. 1997, 38, 2279.
18. Piers, E.; Morton, H. E. J. Org. Chem. 1980, 45, 4263.
19. Piers, E.; Chong, J. M.; Morton, H. E. Tetrahedron Lett. 1981, 22, 4905.
20. Piers, E.; Chong, J. M. J. Chem. Soc., Chem. Commun. 1983, 934.
21. Piers, E.; Chong, J. M.; Keay, B. A. Tetrahedron Lett. 1985, 26, 6265.
22. Piers, E.; Chong, J. M. Can. J. Chem. 1988, 66, 1425.
23. Piers, E.; Chong, J. M.; Morton, H. E. Tetrahedron. 1989, 45, 363.
24. Piers, E.; Wong, T.; Ellis, K. A. Can. J. Chem. 1992, 70, 2058.
25. Thermodynamic and kinetic products in stannylcupration of alkyne correspond to the stannylvinyl cuprate intermediates, see ref 5 and 8. In this paper the corresponding hydrolyzed products are also named thermodynamic and kinetic for greater-convenience.
26. Piers, E.; Morton, H. E.; Chong, J. M. Can. J. Chem. 1987, 65, 78.
27. Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933.
28. See also: Cummins, C. H.; Gordon, E. J. Tetrahedron Lett. 1994, 35, 8133.
29. Aksela, R.; Oehlschlager, A. C. Tetrahedron 1991, 47, 1163.
30. Still, W. C. J. Am. Chem. Soc. 1977, 99, 4836.
31. Betzer, J.-F.; Delaloge, F.; Muller, B.; Pancrazi, A.; Prunet. J. J. Org. Chem. 1997, 62, 7768.
32. 3Li addition to alkyne by: Nozaki, K.; Wakamatsu, K.; Nanaka, T.; Tückmantel, W.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1986, 27, 2007.
33. For germylation of alkynes using a proton source, see: Oda, H.; Morizawa, Y.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 3217.
34. Cox, S.D.; Wudl, F. Organometallics 1983, 2, 184.
35. The use of water as proton source was first evoked by Oshima K.; see ref 11 and 12.
36. 4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on basic silica gel (diethyl ether/petroleum ether 0:100 to 50:50) to give compounds 8 (460 mg, 82% yield) and 9 (91 mg, 16% yield). Compounds 1-10 are described in ref 10.
37. For silylcupration of alkynes see : Fleming, I.; Newton, T. W.; Roessler, F. J. Chem. Soc., Perkin Trans. I 1981, 2527.
38. Fleming, I.; Roessler, F. J. Chem. Soc., Chem. Commun. 1980, 276.
39. Taylor, R. J. K. "Organocopper Reagents : a practical approach" Oxford University Press 1994. See also ref 16
40. 2Si).
41. In some cases, stannylcupration of alkyne functions led to formation of bis-stannyl derivatives: see ref 8, 10 and Zweifel, G.; Leong, W. J. Am. Chem. Soc. 1987, 109, 6409.
42. Oxidative coupling reaction could also take place, see: Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1969, 91, 1851.