Stereoselective synthesis of 3-spiro-α-methylene-γ-butyrolactone oxindoles from Morita-Baylis-Hillman adducts of isatin

Tetrahedron

Volumn 64, Issue 15, 2008, Pages 3322-3330

  Shanmugam, Ponnusamy ^a   Vaithiyanathan, Vadivel ^a  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

Author keywords

Baylis Hillman adduct; Isatin; Lactonization; Spirolactone; Spirooxindole

Indexed keywords

3 SPIRO ALPHA METHYLENE GAMMA BUTYROLACTONE OXINDOLE DERIVATIVE; FORMALDEHYDE; ISATIN; MONTMORILLONITE; OXINDOLE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; LACTONIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONE POT SYNTHESIS; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 39649108839     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.02.002     Document Type: Article

References (43)

1. Booker-Milburn K.I., Fedoulo M., Paknoham S.J., Strachan J.B., Melvilleb J.L., and Voyleb M. Tetrahedron Lett. 41 (2000) 4657
2. Xue J., Zhang Y., Wang X., Fun H.K., and Xu J.-H. Org. Lett. 2 (2000) 2583
3. Tratrat C., Giorgi-Renault S., and Husson H.-P. J. Org. Chem. 65 (2000) 6773
4. Wang L., Zhang Y., Hu H.Y., Fun H.K., and Xu J.-H. J. Org. Chem. 70 (2005) 3850
5. Marti C., and Carreira E.M. Eur. J. Org. Chem. (2003) 2209
6. Toyota M., and Ihara M. Nat. Prod. Rep. 15 (1998) 327
7. Dounary A.B., Hatanaka K., Kodanko J.J., Oestreich M., Pfeifer L.A., and Weiss M.M. J. Am. Chem. Soc. 125 (2003) 6261 and references therein
8. Basavaiah D., and Reddy K.R. Org. Lett. 9 (2007) 57
9. Miyamoto H., Okawa Y., Nakazaki A., and Kobayashi S. Angew. Chem., Int. Ed. 45 (2006) 2274
10. Nair V., Vellalath S., Poonoth M., Mohan R., and Suresh E. Org. Lett. 8 (2006) 507
11. Ding K., Lu Y., Nikolovska-Coleska Z., Wang G., Qiu S., Shangary S., Gao W., Qin D., Stuckey J., Krajewski K., Roller P.P., and Wang S. J. Med. Chem. 49 (2006) 3432
12. Teng, Zhang H., and Mendonca A. Molecules 11 (2006) 700
13. Lo M.M.-C., Neumann C.S., Nagayama S., Perlstein E.O., and Schreiber S.L. J. Am. Chem. Soc. 126 (2004) 16077
14. Hilton S.T., Ho T.C.T., Pljevaljcic G., and Jones K. Org. Lett. 2 (2000) 2639
15. Malinakova H.C., and Liebeskind L.S. Org. Lett. 2 (2000) 4083
16. Nakagawa M., Taniguchi M., Sodeoka M., Ito M., Yamaguchi K., and Hino T. J. Am. Chem. Soc. 105 (1983) 3709
17. Chang K.-T., and Shechter H. J. Am. Chem. Soc. 101 (1979) 5084
18. Huang A., Kodanko J.J., and Overman L.E. J. Am. Chem. Soc. 126 (2004) 14043
19. Bagul T.D., Lakshmaiah G., Kawabata T., and Fuji K. Org. Lett. 4 (2002) 249
20. Dounay A.B., and Overman L.E. Chem. Rev. 103 (2003) 2945
21. Trost B.M., and Frederiksen M.U. Angew. Chem. 117 (2005) 312
22. Angew. Chem., Int. Ed. 44 (2005) 308
23. Yong S.R., Willams M.C., Pyne S.G., Ung A.T., Skelton B.W., White A.H., and Turner P. Tetrahedron 61 (2005) 8120
24. Beccalli E.M., Cleriici F., and Gelmi M.L. Tetrahedron 59 (2003) 4615
25. Kawasaki T., Ogawa A., Terashima R., Saheki T., Ban N., Sekiguchi H., Sakaguchi K., and Sakamoto M. J. Org. Chem. 70 (2005) 2957
26. Mao Z., and Baldwin S.W. Org. Lett. 6 (2004) 2425
27. Somei M., Yamada F., Izumi T., and Nakajou M. Heterocycles 45 (1997) 2327
28. da Silva J.F.M., Garden S.J., and Pinto A.C. J. Braz. Chem. Soc. 12 (2001) 273
29. Basavaiah D., Rao A.J., and Satyanarayana T. Chem. Rev. 103 (2003) 811
30. Derewes S.E., and Roos G.H.P. Tetrahedron 44 (1988) 4653
31. Lee K.Y., Gowrisankar S., and Kim J.N. Bull. Korean Chem. Soc. 26 (2005) 1481
32. Shanmugam P., Vaithiyanathan V., and Baby V. Tetrahedron 62 (2006) 4342
33. Shanmugam P., Vaithiyanathan V., and Baby V. Tetrahedron Lett. 47 (2006) 6851
34. Shanmugam P., Vaithiyanathan V., and Baby V. Aust. J. Chem. 60 (2007) 296
35. Shanmugam P., Baby V., and Vaithiyanathan V. Aust. J. Chem. 60 (2007) 850
36. Shanmugam P., Baby V., and Suchithra M. Org. Lett. 9 (2007) 4095
37. Shanmugam P., Vaithiyanathan V., Baby V., and Suchithra M. Tetrahedron Lett. 48 (2007) 9190
38. Balogh M., and Laszlo P. Organic Chemistry Using Clays (1993), Springer, New York, NY
39. Corma A. Chem. Rev. 95 (1995) 559
40. Chakrabarty M., and Sarkar S. Tetrahedron Lett. 44 (2003) 8131
41. Dintzner M.R., Morse K.M., McClelland K.K., and Coligado D.M. Tetrahedron Lett. 45 (2004) 78
42. CCDC file number No. CCDC 653868 & 653869 contains the supplementary crystallographic data for compounds 4a and 4b.
43. Perrin D.D., and Armearego W.F.L. Purification of Laboratory Chemicals. 3rd ed (1988), Pergamon, New York, NY