Triphenylphosphine-catalyzed [3+2] cycloaddition of allenoate and active olefins: Syntheses of spirooxindole derivatives

Synlett

Volumn , Issue 15, 2011, Pages 2256-2258

  Guo, Shanyan ^a   Wang, Rendong ^a   Li, Jian ^a   Li, Chunju ^a   Deng, Hongmei ^a   Jia, Xueshun ^a,b  

^a SHANGHAI UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

active olefins; allenoate; cycloaddition; oxindoles; spirocycle

Indexed keywords

ACID; ALKENE DERIVATIVE; ALLENOATE; ETHYL 2,3 BUTADIENOATE; MALONONITRILE; METHYLMALONONITRILE; NITRILE; OXINDOLE; SPIROOXINDOLE DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

EID: 80052690210     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0030-1261188     Document Type: Article

References (52)

1. Akai S, Tsujino T, Akiyamna E, Tanimoto K, Naka T, Kita Y, J. Org. Chem. 2004 69 2478
2. Marti C, Carreira E M., Eur. J. Org. Chem. 2003 2209
3. Zhang T Y., Zhang H, Tetrahedron Lett. 2002 43 193
4. Gallagher G, Lavanchi P G., Wilson J W., Hieble J, Demmarinis R M., J. Med. Chem. 1985 28 1533
5. Nagata R, Tokunaga T, Hume W, Umezone T, Okazaki U, Ueki Y, Kumagai K, Hourai S, Nagamine J, Seki H, Taiji M, Noguchi H, J. Med. Chem. 2001 44 4641
6. Williams R M., Cox R J., Acc. Chem. Res. 2003 36 127
7. Galliford C V., Scheidt K A., Angew. Chem. Int. Ed. 2007 46 8748;
8. Angew. Chem. 2007, 119, 8902
9. TrostB M, Jiang C, Synthesis 2006 369
10. Lin H, Danishefsky S J., Angew. Chem. Int. Ed. 2003 42 36;
11. Angew. Chem. 2003, 115, 38
12. Zhou F, Liu Y L., Zhou J, Adv. Synth. Catal. 2010 352 1381
13. For selected examples of total syntheses, see:, Greshock T J., Grubbs A W., Tsukamoto S, Williams R M., Angew. Chem. Int. Ed. 2007 46 2262;
14. Angew. Chem. 2007, 119, 2312
15. Grubbs A W., Artman G D. I. I. I., Tsukamoto S, Williams R M., Angew. Chem. Int. Ed. 2007 46 2257;
16. Angew. Chem. 2007, 119, 2307
17. Greshock T J., Grubbs A W., Jiao P, Wicklow D T., Gloer J B., Williams R M., Angew. Chem. Int. Ed. 2008 47 3573;
18. Angew. Chem. 2008, 120, 3629
19. Trost B M., Cramer N, Bernsmann H, J. Am. Chem. Soc. 2007 129 3086
20. For reviews on phosphine-catalyzed reactions, see:, Lu X, Zhang C, Xu Z, Acc. Chem. Res. 2001 34 535
21. Methot J L., Roush W R., Adv. Synth. Catal. 2004 346 1035
22. Ye L.-W, Zhou J, Tang Y, Chem. Soc. Rev. 2008 37 1140
23. Cowen B J., Miller S J., Chem. Soc. Rev. 2009 38 3102
24. Marinetti A, Voituriez A, Synlett 2010 174
25. For relevant examples, see:, Zhang C, Lu X, J. Org. Chem. 1995 60 2906
26. Xu S, Zhou L, Ma R, Song H, He Z, Chem. Eur. J. 2009 15 8698
27. Henry C E., Kwon O, Org. Lett. 2007 9 3069
28. Dudding T, Kwon O, Mercier E, Org. Lett. 2006 8 3643
29. Xia Y, Liang Y, Chen Y, Wang M, Jiao L, Huang F, Liu S, Li Y, Yu Z.-X, J. Am. Chem. Soc. 2007 129 3470
30. Wallace D J., Sidda R L., Reamer R A., J. Org. Chem. 2007 72 1051
31. Lu X, Lu Z, Zhang X, Tetrahedron 2006 62 457
32. Sampath M, Loh T.-P, Chem. Commun. 2009 1568
33. Zhang C, Lu X, J. Org. Chem. 1995 60 2906
34. Du Y, Lu X, J. Org. Chem. 2003 68 6463
35. Wang J.-C, Krische M J., Angew. Chem. Int. Ed. 2003 42 5855;
36. Angew. Chem. 2003, 115, 6035
37. Pham T Q., Pyne S G., Skelton B W., White A H., J. Org. Chem. 2005 70 6369
38. Xiao H, Chai Z, Zheng C.-W, Yang Y.-Q, Liu W, Zhang J.-K, Zhao G, Angew. Chem. Int. Ed. 2010 49 4467;
39. Angew. Chem. 2010, 122, 4569
40. Fang Y.-Q, Jacobsen E N., J. Am. Chem. Soc. 2008 130 5660
41. Cowen B J., Miller S J., J. Am. Chem. Soc. 2007 129 10988
42. Wilson J E., Fu G C., Angew. Chem. Int. Ed. 2006 45 1426;
43. Angew. Chem. 2006, 118, 1454
44. Zhu X.-F, Lan J, Kwon O, J. Am. Chem. Soc. 2003 125 4716
45. Wurz R P., Fu G C., J. Am. Chem. Soc. 2005 127 12234
46. Tran Y S., Kwon O, Org. Lett. 2005 7 4289
47. Tran Y S., Kwon O, J. Am. Chem. Soc. 2007 129 12632
48. Wang T, Ye S, Org. Lett. 2010 12 4168
49. Li J, Liu Y J., Li C J., Jia X S., Adv. Synth. Catal. 2011 353 913
50. Li J, Li S Y., Li C J., Liu Y J., Jia X S., Adv. Synth. Catal. 2010 352 336
51. Zhao Y N., Li J, Li C J., Yin K, Ye D Y., Jia X S., Green Chem. 2010 12 1370
52. CCDC 763015 for compound 3b contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from the Cambridge Crystal-lographic Data Center via www.ccdc.cam.ac.uk/data-request/cif.