AsPh3-catalyzed ylide cyclopropanation for the synthesis of trisubstituted vinylcyclopropane derivatives

Tetrahedron

Volumn 64, Issue 22, 2008, Pages 5032-5035

  Jiang, Hong ^a   Sun, Xiu Li ^a   Zhu, Chun Ying ^a   Dai, Li Xin ^a   Tang, Yong ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ARSINE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DICARBOXYLIC ACID DERIVATIVE; DIETHYL TRANS 2 (2 BROMOPHENYL) 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIETHYL TRANS 2 (2,4 DICHLOROMOPHENYL) 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIETHYL TRANS 2 (4 BROMOPHENYL) 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIETHYL TRANS 2 (4 NITROPHENYL) 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIETHYL TRANS 2 PHENYL 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIETHYL TRANS 2 STYRYL 3 4 TOLYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL 2 (PHENYL(3 PHENYL 1H PYRAZOL 1 YL)METHYL)MALONATE; DIMETHYL 2 BENZYLIDENEMALONATE; DIMETHYL TRANS 2 (FURAN 2 YL) 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL TRANS 2 (PYRIDIN 2 YL) 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL TRANS 2 ETHYL 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL TRANS 2 ISOBUTYL 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL TRANS 2 ISOPROPYL 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL TRANS 2 PHENYL 3 STYRYLCLOPROPANE 1,1 DICARBOXYLATE; DIMETHYL TRANS 2 STYRYL 3 4 TOLYLCLOPROPANE 1,1 DICARBOXYLATE; ESTER DERIVATIVE; HYDRAZONE DERIVATIVE; MALONIC ACID DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RHODIUM TETRAACETATE; TRIPHENYLARSINE; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOPROPANATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS;

EID: 42749083542     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.03.076     Document Type: Article

References (52)

1. Kang Y.-B., Sun X.-L., and Tang Y. Angew. Chem., Int. Ed. 46 (2007) 3918
2. Korotkov V.S., Larionov O.V., Hofmeister A., Magull J., and de Meijere A. J. Org. Chem. 72 (2007) 7504
3. Korotkov V.S., Larionov O.V., and de Meijere A. Synthesis 21 (2006) 3542
4. Kang Y.-B., Tang Y., and Sun X.-L. Org. Biomol. Chem. 4 (2006) 299
5. Cardona F., and Goti A. Angew. Chem. 117 (2005) 8042
6. Angew. Chem., Int. Ed. 44 (2005) 7832
7. Carson C.A., and Kerr M.A. J. Org. Chem. 70 (2005) 8242
8. Pohlhaus P.D., and Johnson J.S. J. Am. Chem. Soc. 127 (2005) 16014
9. Wurz R.P., and Charette A.B. Org. Lett. 7 (2005) 2313
10. Sibi M.P., Ma Z., and Jasperse C.P. J. Am. Chem. Soc. 127 (2005) 5764
11. Pohlhaus P.D., and Johnson J.S. J. Org. Chem. 70 (2005) 1057
12. Young I.S., and Kerr M.A. Org. Lett. 6 (2004) 139
13. Ganton M.D., and Kerr M.A. J. Org. Chem. 69 (2004) 8554
14. Young I.S., and Kerr M.A. Angew. Chem., Int. Ed. 42 (2003) 3023 For a review on the ring-opening reactions of donor/acceptor-substituted cyclopropanes, see:
15. Reissig H.U., and Zimmer R. Chem. Rev. 103 (2003) 1151
16. For the preparation of vinylcyclopropane 1,1-dicarboxylic esters by intramolecular substitution, please see:
17. Gnamm C., Förster S., Miller N., Brödner K., and Helmchen G. Synlett (2007) 790
18. Miura K., Fujisawa N., Toyohara S., and Hosomi A. Synlett (2006) 1883
19. Ma S., Jiao N., Yang Q., and Zheng Z. J. Org. Chem. 69 (2004) 6463
20. Ma S., Jiao N., Zhao S., and Hou H. J. Org. Chem. 67 (2002) 2837
21. Trost B.M., Tanimori S., and Dunn P.T. J. Am. Chem. Soc. 119 (1997) 2735
22. For the preparation of vinylcyclopropane 1,1-dicarboxylic esters by metal decomposition of diazoalkanes with olefins, please see:
23. Mueller P., Allenbach Y., and Robert E. Tetrahedron: Asymmetry (2003) 779
24. Yang M., Webb T.R., and Livant P. J. Org. Chem. 66 (2001) 4945 For other methods, please see:
25. Georgakopoulou G., Kalogiros C., and Hadjiarapoglou L.P. Synlett (2001) 1843
26. For reviews on the preparation of cyclopropane 1,1-dicarboxylic esters, please see:. Lebel H., Marcoux J.-F., Molinaro C., and Charette A.B. Chem. Rev. 103 (2003) 977
27. Li C.-Y., Wang X.-B., Sun X.-L., Tang Y., Zheng J.-C., Xu Z.-H., Zhou Y.-G., and Dai L.-X. J. Am. Chem. Soc. 129 (2007) 1494
28. Li C.-Y., Sun X.-L., Jing Q., and Tang Y. Chem. Commun. (2006) 2980
29. Ye L.-W., Sun X.-L., Li C.-Y., and Tang Y. J. Org. Chem. 72 (2007) 1335
30. Zheng J.-C., Liao W.-W., Tang Y., Sun X.-L., and Dai L.-X. J. Am. Chem. Soc. 127 (2005) 12222
31. Liao W.-W., Li K., and Tang Y. J. Am. Chem. Soc. 125 (2003) 13030
32. Ye S., Huang Z.Z., Xia C.A., Tang Y., and Dai L.-X. J. Am. Chem. Soc. 124 (2002) 2432
33. Ye S., Yuan L., Huang Z.Z., Tang Y., and Dai L.-X. J. Org. Chem. 65 (2000) 6257
34. Ye S., Tang Y., and Dai L.-X. J. Org. Chem. 66 (2001) 5717
35. Tang Y., Chi Z.-F., Huang Y.-Z., Dai L.-X., and Yu Y.-H. Tetrahedron (1996) 8747
36. Jiang H., Deng X., Sun X., Tang Y., and Dai L.-X. J. Org. Chem. 70 (2005) 10202
37. For arsonium ylide in organic synthesis, please see:
38. Cao P., Li C.-Y., Kang Y.-B., Xie Z., Sun X.-L., and Tang Y. J. Org. Chem. 72 (2007) 6628
39. Habrant D., Stengel B., Meunier S., and Mioskowski C. Chem.-Eur. J. 13 (2007) 5433
40. Dai W.-M., Wu A.-X., and Wu H.-F. Tetrahedron: Asymmetry (2002) 2187
41. Chen Y.-L., Ding W.-Y., Cao W.-G., and Lu C. Synth. Commun. (2002) 1953
42. Dai W.-M., and Lau C.W. Tetrahedron Lett. 42 (2001) 2541
43. Shen Y.-C., and Wang T.-L. J. Fluorine Chem. 82 (1997) 139
44. Moorhoff C.M. J. Chem. Res., Synop. (1997) 130
45. Dai W.-M., Wu J., and Huang X. Tetrahedron: Asymmetry 8 (1997) 1979 For reviews, see:
46. He H.S., Chung C.W.Y., But T.Y.S., and Toy P.H. Tetrahedron (2005) 1385
47. Huang Y.-Z., Shi L.-L., and Zhou Z.-L. Triphenylarsine. In: Paquette L.A. (Ed). Encyclopedia of Reagents for Organic Synthesis (1995), Wiley, New York, NY 5339
48. 3As-catalyzed ylide reactions through decomposition of diazocompound:
49. Zhu S.F., Liao Y.X., and Zhu S.Z. Org. Lett. 6 (2004) 377
50. Aggarwal V.K., Patel M., and Studley J. Chem. Commun. (2002) 1514 For a recent review see:
51. Fulton J.R., Aggarwal V.K., and de Vincente J. Eur. J. Org. Chem. (2005) 1479
52. Doyle M.P., and Yan M. J. Org. Chem. 67 (2002) 602