Lewis acid-mediated reactions of 1-cyclopropyl-2-arylethanone derivatives with diethyl 2-oxomalonate and ethyl 2-oxoacetate

Tetrahedron

Volumn 65, Issue 45, 2009, Pages 9336-9343

  Tang, Xiang Ying ^a   Shi, Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,6 Dioxa spiro 4.4 non 3 en 2 ones; 1 Cyclopropyl 2 arylethanones; Diethyl 2 oxomalonate; Ethyl 2 oxoacetate; Lewis acid

Indexed keywords

1 CYCLOPROPYL 2 PHENYLETHANONE; 2 PHENYL 1 (1 PHENYLCYCLOPROPYL)ETHANONE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; DIETHYL 2 OXOMALONATE; ETHYL 2 OXOACETATE; GAMMA LACTONE DERIVATIVE; GLYOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; LEWIS ACID; MALONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PRIORITY JOURNAL; RING OPENING; SOLVENT EFFECT; SYNTHESIS; TRANSESTERIFICATION;

EID: 70349764471     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.09.003     Document Type: Article

References (52)

1. Reissig H.-U., and Zimmer R. Chem. Rev. 103 (2003) 1151-1196
2. Paquette L.A. Chem. Rev. 86 (1986) 733-750
3. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip Y.-C., Tanko J., and Hudlicky T. Chem. Rev. 89 (1989) 165-198
4. de Meijere A., and Wessjohann L. Synlett (1990) 20-32
5. Kulinkovich O.G. Russ. Chem. Rev. 62 (1993) 839
6. Kulinkovich O.G. Pol. J. Chem. (1997) 849
7. Wenkert E. Acc. Chem. Res. 13 (1980) 27-31
8. Wenkert E. Heterocycles 14 (1980) 1703-1708
9. Seebach D. Angew. Chem. 91 (1979) 259-268
10. Angew. Chem., Int. Ed. Engl. 18 (1979) 239-258
11. Gnad F., and Reiser O. Chem. Rev. 103 (2003) 1603-1624
12. de Meijere A., and Kozhushkov S.I. Eur. J. Org. Chem. (2000) 3809-3822
13. de Meijere A. Top. Curr. Chem. 207 (2000) 89-147
14. de Meijere A. Top. Curr. Chem. 207 (2000) 149-227
15. Danishefsky S. Acc. Chem. Res. 12 (1979) 66-72
16. Rubin M., Rubina M., and Gevorgyan V. Chem. Rev. 107 (2007) 3117-3179
17. Binger P., and Büch H.M. Cyclopropenes and Methylenecyclopropanes as Multifunctional Reagents in Transition Metal Catalyzed Reactions. In: de Meijere A. (Ed). Topics in Current Chemistry Vol. 135 (1987), Springer, Berlin 109-131
18. Noyori R., Odagi T., and Takaya H. J. Am. Chem. Soc. 92 (1970) 5780-5781
19. Lewis R.T., Motherwell W.B., and Shipman M. J. Chem. Soc., Chem. Commun. (1988) 948-950
20. Lautens M., and Ren Y. J. Am. Chem. Soc. 118 (1996) 9597-9605 and references therein
21. Liu L., and Montgomery J. J. Am. Chem. Soc. 128 (2006) 5348-5349
22. Han Z., Uehira S., Tsuritani T., Shinokubo H., and Oshima K. Tetrahedron 57 (2001) 987-995
23. Alper P.B., Meyers C., Lerchner A., Siegel D.R., and Carreira E.M. Angew. Chem., Int. Ed. 38 (1999) 3186-3189
24. Smith III A.B., and Scarborough R.M. Tetrahedron Lett. 19 (1978) 1649-1652
25. Ogoshi H., Setsune J.-I., and Yoshida Z.-I. J. Organomet. Chem. 185 (1980) 95-104
26. Ogoshi H., Kikuchi Y., Yamaguchi T., Toi H., and Aoyama Y. Organometallics 6 (1987) 2175-2178
27. Hwu R.J. J. Chem. Soc., Chem. Commun. (1985) 452-453
28. Bertozzi F., Gustafsson M., and Olsson R. Org. Lett. 4 (2002) 3147-3150
29. Bertozzi F., Gustafsson M., and Olsson R. Org. Lett. 4 (2002) 4333-4336
30. Lautens M., and Han W. J. Am. Chem. Soc. 124 (2002) 6312-6316
31. Lautens M., Han W., and Liu J.H.-C. J. Am. Chem. Soc. 125 (2003) 4028-4029
32. Scott M.E., Han W., and Lautens M. Org. Lett. 6 (2004) 3309-3312
33. Tsuritani T., Yamamoto Y., Kawasaki M., and Mase T. Org. Lett. 11 (2009) 1043-1045
34. Mauleón P., Krinsky J.L., and Toste F.D. J. Am. Chem. Soc. 131 (2009) 4513-4520
35. Pagenkopf B.L., and Morales C.L. Org. Lett. 10 (2008) 157-159
36. Korotkov V.S., Larionov A.H., Hofmeister A., Magull J., and de Meijere A. J. Org. Chem. 72 (2007) 7504-7510
37. Tanaka M., Ubukata M., Matsuo T., Yasue K., Matsuya M., Kajimoto Y., Ogo T., and Inaba T. Org. Lett. 9 (2007) 3331-3334
38. Sliwinska A., Czardybon W., and Warkentin J. Org. Lett. 9 (2007) 695-698
39. Zheng X.M., and Kerr M.A. Org. Lett. 8 (2006) 3777-3779
40. Ivanova O.A., Budynina E.M., Grishin Y.K., Trushikov I.V., and Verteletskii P.V. Angew. Chem. 120 (2008) 1123-1126
41. Angew. Chem., Int. Ed. 47 (2008) 1107-1110
42. Avilov D.V., Malusare M.G., Arslancan E., and Dittmer D.C. Org. Lett. 6 (2004) 2225-2228
43. Yang Y.-H., and Shi M. Org. Lett. 8 (2006) 1709-1712
44. Shi M., Tang X.-Y., and Yang Y.-H. Org. Lett. 9 (2007) 4017-4021
45. Shi M., Tang X.-Y., and Yang Y.-H. J. Org. Chem. 73 (2008) 5311-5318
46. Yang Y.-H., and Shi M. Eur. J. Org. Chem. (2006) 5394-5403
47. Nukina M., and Hirota H. Biosci. Biotechnol. Biochem. 56 (1992) 1158-1159
48. Ackland M.J., Hanson J.R., Hitchcock P.B., and Ratcliffe A.H. J. Chem. Soc., Perkin Trans. 1 (1985) 843-847
49. Engstrom K.M., Mendoza M.R., Navarro-Villalobos M., and Gin D.Y. Angew. Chem., Int. Ed. 40 (2001) 1128-1130
50. Yang Y.-H., and Shi M. J. Org. Chem. 70 (2005) 10082-10085
51. The C-5 position is an activated methylene group because of the two substituents: phenyl and acyl groups.
52. 3 were aryl groups, two products derived from path a and path b were obtained.{A figure is presented}