Hydroxy-assisted catalyst-free Michael addition-dehydroxylation of Baylis-Hillman adducts in poly(ethylene glycol)

Tetrahedron Letters

Volumn 47, Issue 17, 2006, Pages 2981-2984

  Chandrasekhar, S ^a   Saritha, B ^a   Jagadeshwar, V ^a   Narsihmulu, Ch ^a   Vijay, Dolly ^a   Sarma, G Dattatreya ^a   Jagadeesh, B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

MACROGOL; SOLVENT; SULFONE;

ARTICLE; BAYLIS HILLMAN REACTION; CATALYST; HYDROGEN BOND; HYDROXYLATION; MICHAEL ADDITION; RECYCLING;

EID: 33645282789     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.02.104     Document Type: Article

References (44)

1. D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 892
2. E. Ciganek L.A. Paquette Organic Reactions vol. 51 1997 John Wiley and Sons New York 201 350
3. V.K. Aggarwal, I. Emme, and S.Y. Fulford J. Org. Chem. 68 2003 692 700
4. M. Shi, and Y.-M. Xu Angew. Chem., Int. Ed. 41 2002 4507 4510
5. S.E. Drewes, and G.H.P. Roos Tetrahedron 44 1988 4653 4670
6. D. Basavaiah, P.D. Rao, and R.S. Hyma Tetrahedron 52 1996 8001 8062
7. G. Li, H.-X. Wei, J.J. Gao, and T.D. Caputo Tetrahedron Lett. 41 2000 1 5
8. D. Basavaiah, S. Pandiaraju, and K. Padmaja Synlett 1996 393 395
9. S.R.S.S. Kotti, X. Xu, G. Li, and A.D. Headley Tetrahedron Lett. 45 2004 1427 1431
10. J.-Y. Legros, and J.-C. Fiaud Tetrahedron Lett. 31 1990 7453 7456
11. Y. Uozumi, H. Danjo, and T. Hayashi J. Org. Chem. 64 1999 3384 3388
12. D. Bouyssi, P. Gerusz, and G. Balme Eur. J. Org. Chem. 2002 2445 2448
13. G. Ortar Tetrahedron Lett. 44 2003 4311 4314
14. L. Navarre, S. Darses, and J.P. Genet Chem. Commun. 2004 1108 1109
15. D. Basavaiah, and P.K.S. Sarma J. Chem. Soc., Chem. Commun. 1992 955 957
16. H.M.R. Hoffmann, and J. Rabe J. Org. Chem. 50 1985 3849 3859
17. K. Pachamuthu, and Y.D. Vankar Tetrahedron Lett. 39 1998 5439 5442
18. D. Basavaiah, M. Krishnamacharyulu, R.S. Hyma, P.K.S. Sarma, and N. Kumaragurubaran J. Org. Chem. 64 1999 1197 1200
19. D. Basaviah, and T. Satyanarayana Chem. Commun. 2004 32 33
20. P.R. Krishna, R. Sachwani, and V. Kannan Chem. Commun. 2004 2580 2581
21. C. Yu, and L. Hu J. Org. Chem. 67 2002 219 223
22. L.-C. Wang, A.L. Luis, K. Agapiou, H.-Y. Jang, M.J. Mergott, and M.J. Krische J. Am. Chem. Soc. 124 2002 2402 2403
23. R. Racker, K. Doring, and O. Reiser J. Org. Chem. 65 2000 6932 6939
24. S.A. Frank, D.J. Mergott, and W.R. Rousch J. Am. Chem. Soc. 124 2002 2404 2405
25. G. Li, J. Rao, X. WeiII, and M. Enright Org. Lett. 2 2000 617 620
26. A.G.M. Barrett, A.S. Cook, and A. Kamimura Chem. Commun. 1998 2533 2534
27. G.W. Kabalka, B. Venkataiah, and G. Dong Tetrahedron Lett. 44 2003 4673 4675
28. A. Patra, A.K. Roy, B.S. Joshi, R. Roy, S. Batra, and A.P. Bhaduri Tetrahedron 59 2003 663 670
29. R. Aumann, X.L. Fu, C. Holst, and R. Frohlich Organometallics 21 2002 4356 4368
30. M. Shi, and Y.M. Xu Angew. Chem., Int. Ed. 41 2002 4507 4510
31. R. Pathak, A.K. Shaw, and A.P. Bhaduri Tetrahedron 58 2002 3535 3541
32. T. Iwamura, M. Fujita, T. Kawakita, S. Kinoshita, S.-i. Watanabe, and T. Kataoka Tetrahedron 57 2001 8455 8466
33. S. Chandrasekhar, Ch. Narsihmulu, S.S. Sultana, and N.R. Reddy Org. Lett. 4 2002 4399 4401
34. S. Chandrasekhar, Ch. Narsihmulu, S.S. Sultana, and N.R. Reddy Chem. Commun. 2003 1716 1717
35. The same reaction could be performed with similar yields in absolute EtOH, however, with longer reaction time and without recycling.
36. 3); δ 166.0, 160.2, 139.5, 133.5, 129.5, 129.0, 128.8, 128.6, 128.2, 128.0, 121.0, 55.2, 52.5..
37. S. Chandrasekhar, Ch. Narsihmulu, B. Saritha, and S.S. Sultana Tetrahedron Lett. 45 2004 5865 5867
38. D. Basavaiah, K. Muthukumaran, and B. Sreenivasulu Synthesis 2000 545
39. P.H. Manson, and N.D. Esmile Tetrahedron 41 1994 12001
40. P. Shanmugam, and P.R. Singh Synlett 2001 1314
41. D. Basavaiah, P.K.S. Sarma, and N. Kumaragurubaran J. Org. Chem. 64 1999 1197
42. T. Funabiki, H. Hosomi, S. Yoshida, and K. Tarama J. Am. Chem. Soc. 104 1982 1560
43. A. Foucaud, and F. El Guemmout Bull. Soc. Chim. Fr. 1989 403
44. + 283.3684, found 283.3681.