Allenylketenes: Versatile substrates in nucleophilic, electrophilic, and cycloaddition reactions

Synthesis

Volumn , Issue 3, 2000, Pages 457-470

  Huang, Wenwei ^a   Tidwell, Thomas T ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

Addition reactions; Allenes; Cycloaddition; Cyclobutenones; Ketenes; Olefination reactions; Silyl substituents

Indexed keywords

KETENE DERIVATIVE;

ARTICLE; CRYSTAL STRUCTURE; CYCLIZATION; MOLECULAR STABILITY; REACTION ANALYSIS; SYNTHESIS;

EID: 0034006959     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6345     Document Type: Article

References (41)

1. (a) Huang, W.; Fang, D.; Temple, K.; Tidwell, T. T. J. Am. Chem. Soc. 1997, 119, 2832.
2. (b) Gong, L.; McAllister, M. A.; Tidwell, T. T. J. Am. Chem. Soc. 1991, 113, 6021.
3. McAllister, M.A.; Tidwell, T. T. J. Org. Chem. 1994, 59, 4506.
4. Huang, W.; Henry-Riyad, H.; Tidwell, T. T. J. Am. Chem. Soc. 1999, 121, 3939.
5. (a) Allen, A. D.; Colomvakos, J. D.; Diederich, F.; Egle, I.; Hao, X.; Liu, R.; Lusztyk, J.; McAllister, M. A.; Rubin, Y.; Sung, K.; Tidwell, T. T.; Wagner, B.D. J. Am. Chem. Soc. 1997, 119, 12125.
6. (b) Egle, I.; Lai, W.-Y.; Moore, P. A.; Renton, P.; Tidwell, T. T.; Zhao, D.-c. J. Org. Chem. 1997, 61, 18.
7. Colomvakos, J. D.; Egle, I.; Ma, J.; Pole, D. L; Tidwell, T. T. J. Org.Chem. 1996, 61, 9522.
8. Brown, R. S.; Christl, M.; Lough, A. J.; Ma, J.; Peters, E. M.; Peters, K.; Sammtleben, F.; Slebocka-Tilk, H.; Sung, K.; Tidwell, T. T. J. Org. Chem. 1998, 63, 6000.
9. (e) Allen, A.D.; Moore, P. A.; Missiha, S.; Tidwell, T. T. J. Org. Chem. 1999, 64, 4690.
10. (f) Allen, A. D.; Lai, W.-Y.; Ma, J.; Tidwell, T. T. J. Am. Chem. Soc. 1994, 116, 2625.
11. (a) López, S.; Rodríquez, J.; Rey, J. G.; de Lera, A. R. J. Am Chem. Soc. 1996, 118, 1881.
12. (b) Murakami, M.; Amii, H.; Itami, K.; Ito, Y. Angew Chem., Int. Ed. Engl. 1995, 34, 1476.
13. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1997, 119, 2950.
14. Murakami, M.; Itami, K.; Ito, Y. J. Am. Chem. Soc. 1999, 121, 4130.
15. (e) Pasto, D. J.; Kong, W. J. Org. Chem. 1989, 54, 4028.
16. (f) Koop, U.; Handke, G.; Krause, N. Liebigs Ann. 1996, 1487.
17. (a) Saalfranck, R. W.; Welch, A.; Haubner, M.; Bauer, U. Liebigs Ann. 1996, 171.
18. (b) Sigman, M. S.; Eaton, B. E. J. Am. Chem. Soc. 1996, 118, 11783.
19. Pasto, D. J.; Yang, S-H. J. Org. Chem. 1989, 54, 3544.
20. (a) Danheiser, R. L.; Sard, H. J. Org. Chem. 1980, 45, 4810.
21. (b) Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Org. Chem. 1998, 63, 8380.
22. Loebach, J. L.; Bennett, D. M.; Danheiser, R. L. J. Am. Chem. Soc. 1998, 120, 9690.
23. Bennett, D. M.; Okamoto, I.; Danheiser, R. L. Organic Lett. 1999, 1, 641.
24. (e) Machiguchi, T.; Hasegawa, T.; Ishiwata, A.; Terashima, S.; Yamabe, S.; Minato, T. J. Am. Chem. Soc. 1999, 121, 4771.
25. (a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
26. (b) Petasis, N. A.; Hu, Y.-H. J. Org. Chem. 1997, 62, 782.
27. Gleiter, R.; Herb, T.; Hofmann, J. Synlett 1996, 987.
28. Aldrichimica Acta 1993, 26, 14.
29. (e) Peterson, D. J. J. Org. Chem. 1968, 33, 780.
30. (a) Niwayama, S.; Kallel, E. A.; Sheu, C.; Houk, K. N. J. Org. Chem. 1996, 61, 2517.
31. (b) Pavlov, S.; Lacombe, L.; Arsenijevic, V. C. R. Acad. Sci., Ser. C 1974, 278, 529.
32. (a) Vilsmaier, E.; Dittrich, K. H.; Sprügel, W. Tetrahedron Lett. 1974, 3601.
33. (b) Vilsmaier, E.; Schneider, R.; Hader, E. Liebigs Ann. Chem. 1980, 1046.
34. Page, P. C. B.; McKenzie, M. J.; Klair, S. K.; Rosenthal, S. In The Chemistry of Organosilicon Compounds, Vol. 2, Rappoport, Z.; Apeloig, Y.; Eds., Wiley: New York, 1998; Chap. 27.
35. Crandall, J. K.; Sojka, S. A.; Komin, J. B. J. Org. Chem. 1974, 39, 2172.
36. (a) Pommier, A.; Pons, J.-M. Synthesis 1993, 441.
37. (b) Morao, I.; Lecea, B.; Arrieta, A.; Cossio, F. P. J. Am. Chem. Soc. 1997, 119, 816.
38. (a) Clinet, J.-C.; Duñach, E.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6710.
39. (b) Butenschön, H.; Winkler, M.; Vollhardt, K. P. C. J. Chem. Soc., Chem. Commun. 1986, 388.
40. Pons, J.-M.; Oblin, M.; Pommier, A.; Rajzmann, M.; Liotard, D. J. Am. Chem. Soc. 1997, 119, 3333.
41. Crystallographic data for 18c, 29, and 31a have been deposited with the Cambridge Crystallographic Data Centre, deposition numbers 137453-137455, and copies of this data can be obtained in application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax +44 1223-336-033; E-mail: deposit@ccdc.cam.ac.uk).