Stereoselective synthesis of geometrically strained, oxindole-appended vinyl cyclopropanes and highly substituted cyclopentenes via sulfur ylide cyclopropanation and vinyl cyclopropane rearrangement

Synlett

Volumn , Issue 2, 2012, Pages 278-284

  Lingam, Kandapalam Arun Prasath ^a   Shanmugam, Ponnusamy ^a   Selvakumar, Kodirajan ^b  

^a CENTRAL LEATHER RESEARCH INSTITUTE   (India)

^b REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

3+2 cycloaddition; diastereoselective synthesis; vinyl cyclopropane rearrangement; vinyl cyclopropanes

Indexed keywords

CYCLOPENTENE DERIVATIVE; CYCLOPROPANE; ISATIN; OXINDOLE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLOADDITION; CYCLOPROPANATION; EPIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 84855858016     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0031-1290077     Document Type: Article

References (49)

1. Pietruszka J, Chem. Rev. 2003 103 1051
2. Wessjohann L A., Brandt W, Chem. Rev. 2003 103 1625
3. Brackmann F, DeMeijere A, Chem. Rev. 2007 107 4538
4. Trost B M., Yasukata T, J. Am. Chem. Soc. 2001 123 7162
5. Wender P A., Barziay C M., Dyckman A, [nl]J. Am. Chem. Soc. 2001 123 179
6. Sebelius S, Olsson V J., Szabo K J., J. Am. Chem. Soc. 2005 127 10478
7. Xie H, Zu L, Li H, Wang J, Wang W, J. Am. Chem. Soc. 2007 129 10886
8. Li A.-H, Dai L.-X, Aggarwal V K., Chem. Rev. 1997 97 2341
9. Rubin M, Rubina M, Gevorgyan V, Chem. Rev. 2007 107 3117
10. Lebel H, Marcoux J.-F, Molinaro C, Charette A B., Chem. Rev. 2003 103 977
11. Jiang H, Deng X, Sun X, Tang Y, Dai L.-X, J. Org. Chem. 2005 70 10202
12. Ye S, Huang Z Z., Xia C A., Tang Y, Dai L.-X, J. Am. Chem. Soc. 2002 124 2432
13. Carson C A., Kerr M A., Chem. Soc. Rev. 2009 38 3051
14. Oba M, Nishiyama N, Nishiyama K, Tetrahedron 2005 61 8456
15. Brichacek M, Lee D, Njardarson J T., Org. Lett. 2008 10 5023
16. Pellissier H, Tetrahedron 2008 64 7041
17. Zhu [nl]B.-H, Zheng J.-C, Yu C.-B, Sun X.-L, Zhou Y.-G, Shen Q, Tang Y, Org. Lett. 2010 12 504
18. Yang X F., Zhang M J., Hou X.-L, Dai L.-X, J. Org. Chem. 2002 67 8097
19. Aggarwal V K., Winn C L., Acc. Chem. Res. 2004 37 611
20. Reissig H.-U, Zimmer R, Chem. Rev. 2003 103 1151
21. Brichacek M, Villalobos M N., Plichta A, Njardarson J T., Org. Lett. 2011 13 1110
22. Fontana F, Chen C.-C, Aggarwal V K., Org. Lett. 2011 13 3454
23. Trost B M., Fandrick D R., J. Am. Chem. Soc. 2003 125 11836
24. Trost B M., Morris P J., Angew. Chem. Int. Ed. 2011 50 6167
25. Galliford C V., Scheidt K A., Angew. Chem. Int. Ed. 2007 46 8748
26. Parsons A T., Campbell M J., Johnson J S., Org. Lett. 2008 10 2541
27. Singh A, Roth G P., Org. Lett. 2011 13 2118
28. Liu T.-L, Xue Z.-Y, Tao H.-Y, Wang C.-J, Org. Biomol. Chem. 2011 9 1980
29. Cheng M N., Wang H, Gong L Z., Org. Lett. 2011 13 2418
30. Zhong F, Chen G Y., Lu Y, Org. Lett. 2011 13 82
31. Deng H.-P, Wei Y, Shi M, Org. Lett. 2011 13 3348
32. Tan B, Candeias N R., Barbas C F. III., J. Am. Chem. Soc. 2011 133 4672
33. Viswambharan B, Selvakumar K, Suchithra M, Shanmugam P, Org. Lett. 2010 12 2108
34. Selvakumar K, Vaithiyanathan V, Shanmugam P, Chem. Commun. 2010 46 2826
35. Lingam K A. P., Mandal A B., Shanmugam P, Tetrahedron Lett. 2011 52 3610
36. Baldwin J E., Chem. Rev. 2003 103 1197
37. Davies H M. L., Kong N, Churchill M R., J. Org. Chem. 1998 63 6586
38. Hudlicky T, Reed J W., Angew. Chem. Int. Ed. 2010 49 4864
39. Cowen B J., Miller S J., Chem. Soc. Rev. 2009 38 3102
40. Zhang X.-C, Cao S.-H, Wei Y, Shi M, Chem. Commun. 2010 47 1548
41. Bond R F., Boeyens J C. A., Holzapfel C W., Steyn P S., J. Chem. Soc., Perkin Trans. 1 1979 1751
42. Greshock T J., Grubbs A W., Jiao P, Wicklow D T., Gloer J B., Williams R M., Angew. Chem. Int. Ed. 2008 47 3573
43. Appel R, Hartmann N, Mayr H, J. Am. Chem. Soc. 2010 132 17894
44. Lemek T, Mayr H, J. Org. Chem. 2003 68 6880
45. Pohlhaus P D., Sanders S D., Parsons A T., Li W, Johnson J S., J. Am. Chem. Soc. 2008 130 8642
46. Armesto D, Ramos A, Mayoral E P., Ortiz M J., Agarrabeitia A R., Org. Lett. 2000 2 183
47. Houk K N., Nendel M, Wiest O, Storer J W., J. Am. Chem. Soc. 1997 119 10545
48. Zhang X.-C, Cao S.-H, Wei Y, Shi M, Org. Lett. 2011 13 1142
49. Chen X.-Y, Wen M.-W, Ye S, Wang Z.-X, Org. Lett. 2011 13 1138