Lewis acid mediated reactions of cyclopropyl aryl ketones with α-ketoesters: Facile preparation of 5,6-dihydropyran-2-ones

Journal of Organic Chemistry

Volumn 70, Issue 24, 2005, Pages 10082-10085

  Yang, Yong Hua ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION ANALYSIS; ESTERIFICATION; ESTERS; ORGANIC ACIDS; REACTION KINETICS;

CYCLOPROPANE; LEWIS ACID; RING-OPENING REACTION; TRANSESTERIFICATION;

KETONES;

5,6 DIHYDROPYRAN 2 ONE; CYCLOPROPANE; ESTER DERIVATIVE; FREE RADICAL; LEWIS ACID; PYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; DERIVATIZATION; ELECTRON TRANSPORT; REACTION ANALYSIS; RING OPENING; TRANSESTERIFICATION;

EID: 28044442730     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051815z     Document Type: Article

References (38)

1. (a) Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151.
2. (b) Paquette, L. A. Chem. Rev. 1986, 86, 733.
3. (c) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165.
4. (d) de Meijere, A.; Wessjohann, L. Synlett 1990, 20.
5. (e) Kulinkovich, O. G. Russ. Chem. Rev. 1993, 62, 839.
6. (f) Kulinkovich, O. G. Pol. J. Chem. 1997, 849.
7. (g) Wenkert, E. Acc. Chem. Res. 1980, 13, 27.
8. (h) Wenkert, E. Heterocycles 1980, 14, 1703.
9. (i) Seebach, D. Angew. Chem. 1979, 91, 259;
10. Angew. Chem., Int. Ed. 1979, 18, 239.
11. (j) Gnad, F.; Reiser, O. Chem. Rev. 2003, 103, 1603.
12. (a) Danishefsky, S. Acc. Chem. Res. 1979, 12, 66.
13. (b) Avilov, D. V.; Malusare, M. G.; Arslancan, E.; Dittmer, D. C. Org. Lett. 2004, 6, 2225.
14. (a) Han, Z.; Uehira, S.; Tsuritani, T.; Shinokubo, H.; Oshima, K. Tetrahedron 2001, 57, 987.
15. (b) Alper, P. B.; Meyers, C.; Lerchner, A.; Siegel, D. R.; Carreira, E. M. Angew. Chem., Int. Ed. 1999, 38, 3186.
16. (c) Smith, A. B., III; Scarborough, R. M. Tetrahedron Lett. 1978, 19, 1649.
17. (d) Ogoshi, H.; Setsune, J.-I.; Yoshida, Z.-I. J. Organomet. Chem. 1980, 185, 95.
18. (e) Ogoshi, H.; Kikuchi, Y.; Yamaguchi, T.; Toi, H.; Aoyama, Y. Organometallics 1987, 6, 2175.
19. (f) Ru Hwu, J. Chem. Commun. 1985, 452.
20. (g) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 3147.
21. (h) Bertozzi, F.; Gustafsson, M.; Olsson, R. Org. Lett. 2002, 4, 4333.
22. Lautens, M.; Han, W. J. Am. Chem. Soc. 2002, 124, 6312.
23. (j) Lautens, M.; Han, W.; Liu, J. H.-C. J. Am. Chem. Soc. 2003, 125, 4028.
24. (k) Scott, M. E.; Han, W.; Lautens, M. Org. Lett. 2004, 6, 3309.
25. (a) Lim, Y.-H.; McGee, K. F., Jr.; Sieburth, S. M. J Org. Chem. 2002, 67, 6535.
26. (b) Yates, P.; Helferty, H.; Mahier, P. Can. J. Chem. 1983, 61, 78.
27. Demuth, M.; Raghavan, P. R. Helv. Chim. Acta 1979, 62, 2338.
28. Yadav, V. K.; Balamurugan, R. Org. Lett. 2003, 5, 4281.
29. (a) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 5248.
30. (b) Enholm, E. J.; Jia, Z. J. J. Org. Chem. 1997, 62, 9159.
31. Batey, R. A.; Motherwell, W. B. Tetrahedron Lett. 1991, 32, 6649.
32. Batey, R. A.; Harling, J. D.; Motherwell, W. B. Tetrahedron 1996, 52, 11421.
33. Shi, M.; Yang, Y.-H.; Xu, B. Tetrahedron 2005, 61, 1893.
34. (a) Takaya, Y.; Kikuchi, H.; Term, Y.; Komiya, J.; Furukawa, K.-I.; Seya, K.; Motomura, S.; Ito, A.; Oshima, Y. J. Org. Chem. 2000, 65, 985.
35. (b) Giorgio, E.; Maddau, L.; Spanu, E.; Evidente, A.; Rosini, C. J. Org. Chem. 2005, 70, 7.
36. (c) Akiyama, K.; Yamamoto, S.; Fujimoto, H.; Ishibashi, M. Tetrahedron 2005, 61, 1827.
37. (d) Chandrasekhar, S.; Narsihmulu, C.; Shameem Sultama, S.; Srinivasa Reddy, M. Tetrahedron Lett. 2004, 45, 9299.
38. (e) Iqbal Choudhary, M.; Yousuf, S.; Ahmad Nawaz, S.; Ahmed, S.; Atta-Ur-Rahman Chem. Pharm. Bull. 2004, 52, 1358.