Stannylcupration of acetylenes followed by reaction with epoxides: A novel annulation strategy for the synthesis of cyclobutenes

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7531-7533

  Barbero, Asunción ^a   Cuadrado, Purificación ^a   García, Carlos ^a   Rincón, Juan A ^a   Pulido, Francisco J ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001486879     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980874s     Document Type: Article

References (58)

1. SiCu of allenes and acetylenes: (a) Fleming, I.; Pulido, F. J. J. Chem. Soc., Chem. Commun. 1986, 1010.
2. (b) Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. Tetrahedron. Lett. 1988, 29, 1825.
3. Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I.; Rowley, M. Tetrahedron 1989, 45, 413.
4. Barbero, A.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1991, 2811.
5. (e) Blanco, F. J.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. Tetrahedron Lett. 1994, 35, 8881.
6. (f) Barbero, A.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I.; Sánchez, A. J. Chem. Soc., Perkin Trans. 1 1995, 1525.
7. (g) Blanco, F. J.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J. Synthesis 1996, 42.
8. SnCu of allenes: (a) Barbero, A.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. J. Chem. Soc., Chem. Commun. 1990, 1030.
9. (b) Barbero, A.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1992, 327.
10. Barbero, A.; Cuadrado, P.; Gonzalez, A. M.; Pulido, F. J.; Fleming, I. J. Chem. Res. 1990, 297, 291.
11. See also ref 1c.
12. (a) Sharma, S.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 770.
13. (b) Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Org. Chem. 1991, 56, 4933.
14. Singer, R. D.; Hutzinger, M. W.; Oehlschlager, A. C. J. Am. Chem. Soc. 1990, 112, 9397.
15. Piers, E.; Gavai, A. V. J. Org. Chem. 1990, 55, 2374 and 2380.
16. (e) Piers, E.; Chong, J. M. Can. J. Chem. 1988, 66, 1425.
17. (f) Cox, S. D.; Wudl, F. Organometallics 1983, 2, 184.
18. (g) Lipshutz, B. H.; Sharma, S.; Reuter, D. C. Tetrahedron Lett. 1990, 31, 7253.
19. (h) Lipshutz, B. H.; Reuter, D. C. Tetrahedron Lett. 1989, 30, 4617 and 2065.
20. Magriotis, P. A.; Scott, M. E.; Kim, K. D. Tetrahedron Lett. 1991, 32, 6085.
21. (j) Marino, J. P.; Edmonds, M. V. M.; Stengel, P. J.; Oliveira, A. R. M.; Simonelli, F.; Ferreira, J. T. B. Tetrahedron Lett. 1992, 33, 49.
22. (k) Beaudet, I.; Parrain, J. L.; Quintard, J. P. Tetrahedron Lett. 1991, 32, 6333.
23. Marek, I.; Alexakis, A.; Normant, J. F. Tetrahedron Lett. 1991, 32, 6337.
24. Pereira, O. Z.; Chan, T. H. Tetrahedron Lett. 1995, 36, 8749.
25. (n) Pereira, O. Z.; Chan, T. H. J. Org. Chem. 1996, 61, 5406.
26. (o) See also ref le and citations therein.
27. (a) Sharma, S.; Oehlschlager, A. C. Tetrahedron Lett. 1986, 27, 6161.
28. (b) Sharma, S.; Oehlschlager, A. C. Tetrahedron Lett. 1988, 29, 261.
29. Nozaki, K.; Wakamatsu, K.; Nonaka, T.; Tückmantel, W.; Oshima, K.; Utimoto, K. Tetrahedron Lett. 1986, 27, 2007.
30. Nonaka, T.; Okuda, Y.; Matsubara, S.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1986, 51, 4716.
31. (e) Mitchell, T. N.; Wickenkamp, R.; Amaria, A.; Dicke, R.; Schneider, U. J. Org. Chem. 1987, 52, 4868.
32. (f) Mitchell, T. N. J. Organomet. Chem. 1992, 437, 127.
33. (g) See also ref 1c and citations therein.
34. Morizawa, Y.; Oda, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 1163.
35. SnCu of acetylenes: (a) Barbero, A.; Cuadrado, P.; González, A. M.; Pulido, F. J.; Fleming, I. J. Chem. Soc., Chem. Commun. 1992, 351.
36. (b) Barbero, A.; Cuadrado, P.; González, A. M.; Pulido, F. J.; Rubio, R.; Fleming, I. J. Chem. Soc., Perkin Trans. 1 1993, 1657.
37. (a) Fuks, R.; Viehe, H. G. In Chemistry of Acetylenes; Viehe, H. G., Ed.; Dekker: New York, 1969; p 434.
38. (b) Cargill, R. L.; Beckham, M. E.; Siebert, A. E.; Dorn, J. J. Org. Chem. 1965, 30, 3647.
39. Scharf, H. D.; Mattay, J. Justus Liebigs Ann. Chem. 1977, 772.
40. (a) Vos, G. J. M.; Benders, P. H.; Reinhoudt, D. N.; Egberink, R. J. M.; Harkema, S.; Van Hummel, G. J. J. Org. Chem. 1986, 51, 2004.
41. (b) Cook, A. G. In Enamines: Synthesis, Structure and Reactions; Cook, A. G., Ed.; Dekker: New York, 1988.
42. Ficini, J.; d'Angelo, J. Tetrahedron Lett. 1976, 687.
43. Carbocyclic Four-Membered Ring Compounds, Houben-Weyl Methods of Organic Chemistry; deMeijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. 17f, E17e-f.
44. (a) Paquette, L. A. Acc. Chem. Res. 1968, 1, 209.
45. (b) Paquette, L. A.; Photis, J. M. J. Am. Chem. Soc. 1974, 96, 4715.
46. (a) Aben, R. W.; Scheeren, H. W. J. Chem. Soc., Perkin Trans. 1 1979, 3132.
47. (b) Halazy, S.; Krief, A. Tetrahedron Lett. 1980, 21, 1997.
48. Sohn, M. B.; Jones, M., Jr. J. Am. Chem. Soc. 1972, 94, 8280.
49. (a) Vincens, M.; Dumont, C.; Vidai, M. Bull. Soc. Chim. Fr. 1984, Part 2, 59.
50. (b) Vincens, M.; Dumont, C.; Vidai, M. Tetrahedron Lett. 1986, 27, 2267.
51. (a) Pettit, R.; Henery, J. Org. Synth. 1970, 50, 36.
52. (b) Vogel, E.; Hasse, K. Justus Liebigs Ann. Chem. 1958, 615, 22.
53. Negishi, E.; Boardman, L. D.; Sawada, H.; Bagheri, V.; Stoll, A. T.; Tour, J. M.; Rand, C. L. J. Am. Chem. Soc. 1988, 110, 5383.
54. Barbero, A.; Cuadrado, P.; González, A. M.; Pulido, F. J.; Rubio, R.; Fleming, I. Tetrahedron Lett. 1992, 33, 5841.
55. 2O, the reaction gives poor yields.
56. A typical reaction using diphenylacetylene led to only a 15% of 1,2-diphenylcyclobutene.
57. Wilt, J. W.; Roberts, D. D. J. Org. Chem. 1962, 27, 3430.
58. Schweizer, E. E.; Thompson, J. G.; Ulrich, T. A. J. Org. Chem. 1968, 33, 3082.