SnCl4-mediated reactions of cyclopropyl alkyl ketones with α-keto esters

European Journal of Organic Chemistry

Volumn , Issue 23, 2006, Pages 5394-5403

  Yang, Yong Hua ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

keto esters; Cyclopropyl alkyl ketones; Lewis acids; Spiro lactones

Indexed keywords

EID: 33845438958     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600618     Document Type: Article

References (50)

1. a) H.-U. Reissig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196;
2. b) L. A. Paquette, Chem. Rev. 1986, 86, 733-750;
3. c) H. N. C. Wong, M.-Y. Hon, C.-W. Tse, Y.-C. Yip, J. Tanko, T. Hudlicky, Chem. Rev. 1989, 89, 165-198;
4. d) A. de Meijere, L. Wessjohann, Synlett 1990, 20-32;
5. e) O. G. Kulinkovich, Russ. Chem. Rev. 1993, 62, 839-850;
6. f) O. G. Kulinkovich, Pol. J. Chem. 1997, 71, 849-882;
7. g) E. Wenkert, Acc. Chem. Res. 1980, 13, 27-31;
8. h) E. Wenkert, Heterocycles 1980, 14, 1703-1708;
9. i) D. Seebach, Angew. Chem. 1979, 91, 259-278;
10. Angew. Chem. Int. Ed. Engl. 1979, 18, 239-258;
11. j) F. Gnad, O. Reiser, Chem. Rev. 2003, 103, 1603-1623;
12. k) A. de Meijere, S. I. Kozhushkov, Eur. J. Org. Chem. 2000, 3809-3822;
13. l) A. de Meijere, Top. Curr. Chem. 2000, 207, 89-147;
14. m) A. de Meijere, Top. Curr. Chem. 2000, 207, 149-227.
15. a) S. Danishefsky, Acc. Chem. Res. 1979, 12, 66-72;
16. b) D. V. Avilov, M. G. Malusare, E. Arslancan, D. C. Dittmer, Org. Lett. 2004, 6, 2225-2228.
17. a) Z. Han, S. Uehira, T. Tsuritani, H. Shinokubo, K. Oshima, Tetrahedron 2001, 57, 987-995;
18. b) P. B. Alper, C. Meyers, A. Lerchner, D. R. Siegel, E. M. Carreira, Angew. Chem. Int. Ed. 1999, 38, 3186-3189;
19. c) A. B. Smith III, R. M. Scarborough, Tet. Lett. 1978, 19, 1649-1652;
20. d) H. Ogoshi, J.-I. Setsune, Z.-I. Yoshida, J. Organomet. Chem. 1980, 185, 95-104;
21. e) H. Ogoshi, Y. Kikuchi, T. Yamaguchi, H. Toi, Y. Aoyama, Organometallics 1987, 6, 2175-2178;
22. f) R. J. Hwu, J. Chem. Soc., Chem. Commun. 1985, 452-453;
23. g) F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 3147-3150;
24. h) F. Bertozzi, M. Gustafsson, R. Olsson, Org. Lett. 2002, 4, 4333-4336;
25. i) M. Lautens, W. Han, J. Am. Chem. Soc. 2002, 124, 6312-6316;
26. j) M. Lautens, W. Han, J. H.-C. Liu, J. Am. Chem. Soc. 2003, 125, 4028-4029;
27. k) M. E. Scott, W. Han, M. Lautens, Org. Lett. 2004, 6, 3309-3312.
28. a) Y.-H. Lim, K. F. McGee, S. McN. Sieburth, J. Org. Chem. 2002, 67, 6535-6538;
29. b) P. Yates, P. H. Helferty, P. Mahler, Can. J. Chem. 1983, 61, 78-85;
30. c) M. Demuth, P. R. Raghavan, Helv. Chim. Acta 1979, 62, 2338-2349.
31. V. K. Yadav, R. Balamurugan, Org. Lett. 2003, 5, 4281-4284.
32. a) E. J. Enholm, Z. J. Jia, J. Org. Chem. 1997, 62, 5248-5249;
33. b) E. J. Enholm, Z. J. Jia, J. Org. Chem. 1997, 62, 9159-9164;
34. c) R. A. Batey, W. B. Motherwell, Tet. Lett. 1991, 32, 6649-6652;
35. d) R. A. Batey, J. D. Harling, W. B. Motherwell, Tetrahedron 1996, 52, 11421-11444.
36. a) S. Ogoshi, M. Nagata, H. Kurosawa, J. Am. Chem. Soc. 2006, 128, 5348-5349;
37. b) L. Liu, J. Montgomery, J. Am. Chem. Soc. 2006, 128, 5350-5351.
38. Y.-H. Yang, M. Shi, J. Org. Chem. 2005, 70, 10082-10085.
39. a) Y. Takaya, H. Kikuchi, Y. Terui, J. Komiya, K.-I. Furukawa, K. Seya, S. Motomura, A. Ito, Y. Oshima, J. Org. Chem. 2000, 65, 985-989;
40. b) E. Giorgio, L. Maddau, E. Spanu, A. Evidente, C. Rosini, J. Org. Chem. 2005, 70, 7-13;
41. c) K. Akiyama, S. Yamamoto, H. Fujimoto, M. Ishibashi, Tetrahedron 2005, 61, 1827-1833;
42. d) S. Ghandrasekhar, Ch. Narsihmulu, S. S. Sultama, M. S. Reddy, Tet. Lett. 2004, 45, 9299-9301;
43. e) M. I. Choudhary, S. Yousuf, S. A. Nawaz, S. Ahmed, Atta-Ur-Rahman, Chem. Pharm. Bull. 2004, 52, 1358-1361.
44. Y.-H. Yang, M. Shi, Org. Lett. 2006, 8, 1709-1712. The X-ray crystal structure of 6c is reported in this reference.
45. 3; F(000) = 1232; R1 = 0.0458, wR2 = 0.1010. Diffractometer: Rigaku AFC7R. CCDC-287397 (for 6b), -29384 (for 4c) and - 297742 (for 5c) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
46. a) C. U. Pittman, S. P. McManus, J. Am. Chem. Soc. 1969, 91, 5815-5818;
47. b) P. J. Ranfaing, G. Combaut, L. Giral, Bull. Soc. Chim. Fr. 1974, 1048-1052.
48. 3; F(000) = 768; R1 = 0.0654, wR2 = 0.1746. Diffractometer: Rigaku AFC7R.
49. a) C. K. Bradsher, J. Am. Chem. Soc. 1940, 62, 486-488;
50. b) C. K. Bradsher, E. F. Sinclair, J. Org. Chem. 1957, 22, 79-81.