A New and Practical Five-Carbon Component for Metal-Catalyzed [5 + 2] Cycloadditions: Preparative Scale Syntheses of Substituted Cycloheptenones

Organic Letters

Volumn 2, Issue 11, 2000, Pages 1609-1611

  Wender, Paul A ^a   Dyckman, Alaric J ^a   Husfeld, Craig O ^a   Scanio, Marc J C ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001301163     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0058691     Document Type: Article

References (27)

1. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Frühauf, H.-W. Chem. Rev. 1997, 97, 523-569. Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765-769.
2. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Frühauf, H.-W. Chem. Rev. 1997, 97, 523-569. Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765-769.
3. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Frühauf, H.-W. Chem. Rev. 1997, 97, 523-569. Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765-769.
4. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Frühauf, H.-W. Chem. Rev. 1997, 97, 523-569. Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765-769.
5. Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92. Frühauf, H.-W. Chem. Rev. 1997, 97, 523-569. Dell, C. P. J. Chem. Soc., Perkin Trans. 1 1998, 3873-3905. Wender, P. A.; Miller, B. L. Toward the Ideal Synthesis: Connectivity Analysis and Multibond-Forming Processes. In Organic Synthesis: Theory and Applications; Hudlicky, T., Ed.; JAI Press: Greenwich, CT, 1993; Vol. 2, pp 27-66. Wender, P. A.; Handy, S. T.; Wright, D. L. Chem. Ind. 1997, 765-769.
6. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
7. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
8. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
9. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
10. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
11. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
12. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
13. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
14. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
15. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
16. Wender, P. A.; Takahashi, H.; Witulski, B. J. Am. Chem. Soc. 1995, 117, 4720-4721. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1998, 120, 1940-1941. Wender, P. A.; Husfeld, C. O.; Langkopf, E.; Love, J. A. Pleuss, N. Tetrahedron 1998, 54, 7203-7220. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977. Wender, P. A.; Sperandio, D. J. Org. Chem. 1998, 63, 4164-4165. Wender, P. A.; Glorius, F.; Husfeld, C. O.; Langkopf, E.; Love, J. A. J. Am. Chem. Soc. 1999, 121, 5348-5349. Wender, P. A.; Fuji, M.; Husfeld, C. O.; Love, J. A. Org. Lett 1999, 1, 137-139. Wender, P. A.; Dyckman, A. J.; Husfeld, C. O.; Kadereit, D.; Love, J. A.; Rieck, H. J. Am. Chem. Soc. 1999, 121, 10442-10443. For recent studies from other laboratories see: Gilbertson, S. R.; Hoge, G. S. Tetrahedron Lett. 1998, 39, 2075-2078. Binger, P. Wedemann, P. Kozhushkov, S. I. de Meijere, A. Eur. J. Org. Chem. 1998, 113-119. Trost, B. M.; Toste, F. D.; Shen, H. J. Am. Chem. Soc. 2000, 122, 2379-2380.
17. Wender, P. A.; Fuji, M., Husfeld, C. O., Love, J. A. Org. Lett. 1999, 1, 137-139.
18. Wender, P. A.; Rieck, H.; Fuji, M. J. Am. Chem. Soc. 1998, 120, 10976-10977.
19. Preparation of 5 by analogy to the methods in the following: Salaün, J.; Marguerite, J. Org. Synth. 1985, 63, 147-153. Wasserman, H. H.; Hearn, M. J.; Cochoy, R. E. J. Org. Chem. 1980, 45, 2874-2880.
20. Preparation of 5 by analogy to the methods in the following: Salaün, J.; Marguerite, J. Org. Synth. 1985, 63, 147-153. Wasserman, H. H.; Hearn, M. J.; Cochoy, R. E. J. Org. Chem. 1980, 45, 2874-2880.
21. Overman, L. E.; Kakimoto, M.; Okazaki, M. E.; Meier, P. G. J. Am. Chem. Soc. 1983, 105, 6622-6629. Original work using N-bromosulfonamides: Petrov J. Gen. Chem. U.S.S.R. 1938, 8, 208-212.
22. Overman, L. E.; Kakimoto, M.; Okazaki, M. E.; Meier, P. G. J. Am. Chem. Soc. 1983, 105, 6622-6629. Original work using N-bromosulfonamides: Petrov J. Gen. Chem. U.S.S.R. 1938, 8, 208-212.
23. Caution. It is important to add the KOH slowly due to the exothermic nature of the reaction causing excess 1,3-butadiene to rapidly boil out of solution at approximately 40°C.
24. 4), filtered, and condensed by rotoary evaporation. Distillation of the product (10 torr, 60°C) affords diene 7 in 44-57% yield as a colorless oil.
25. Friedrich, E. C.; Lewis, E. J. J. Org. Chem. 1990, 55, 2491-2494.
26. On the basis of the price of reagents purchased from Aldrich in 1999, 9 cost $211.88/mol ($1.49/g) and 5 cost $2785.25/mol ($14.04/g).
27. 2O eluant) and concentrated in vacuo. The residue was purified by flash column chromatography.