Efficient Horner-Wadsworth-Emmons intramolecular cyclisation of a N-substituted phthalimide promoted by KF-Alumina: a general tool for the synthesis of functionalised isoindolinones

Tetrahedron Letters

Volumn 50, Issue 25, 2009, Pages 3050-3053

  Pace, Vittorio ^a   Martínez, Fernando ^a   Nova, Clara I ^b   Fernández, María ^a   Sinisterra, José Vicente ^a,b   Alcántara, Andrés R ^a,b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b Industrial Biotransformations Service   (Spain)

Author keywords

Cyclisation; Enones; Heterogeneous catalysis; Horner Wadsworth Emmons reaction; Isoindolinones

Indexed keywords

ALUMINUM OXIDE; PHTHALIMIDE;

ALKYLATION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; HORNER WADSWORTH EMMONS REACTION; SYNTHESIS; WITTIG REACTION;

EID: 65449141617     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.04.029     Document Type: Article

References (54)

1. Valencia E., Fajardo V., Freyer A.J., and Shamma M. Tetrahedron Lett. 26 (1985) 993-996
2. Zhuang Z.-P., Kung M.-P., Mu M., and Kung J. J. Med. Chem. 41 (1998) 157-166
3. Norman M.H., Minick D.J., and Rigdon G.C. J. Med. Chem. 39 (1996) 149-157
4. Taylor E.C., Zhou P., Jennings L.D., Mao Z., Hu B., and Jun J.-G. Tetrahedron Lett. 38 (1997) 521-524
5. Yao T., and Larock R.C. J. Org. Chem. 70 (2005) 1432-1437
6. Watanabe H., Mao C.-L., Barnish I.T., and Hauser C.R. J. Org. Chem. 34 (1969) 919-924
7. Parham W.E., and Jones L.D. J. Org. Chem. 41 (1976) 1188-1191
8. Couture A., Deniau E., and Grandclaudon P. Tetrahedron 53 (1997) 10313-10330
9. Couture A., Deniau E., Ionescu D., and Grandclaudon P. Tetrahedron Lett. 39 (1998) 2319-2320
10. Gutiérrez A.J., Shea K.J., and Svoboda J.J. J. Org. Chem. 54 (1989) 4335-4344
11. Guillaumel J., Boccara N., Demersemann P., and Royer R. J. Chem. Soc., Chem. Commun. (1988) 1604-1605
12. Freccero M., Fasani E., and Albini A. J. Org. Chem. 58 (1993) 1740-1745
13. Weidner-Wells M.A., Oda K., and Mazzocchi P.H. Tetrahedron 53 (1997) 3475-3486
14. Brewster J.H., Fusco A.M., Carosino L.E., and Corman B.G. J. Org. Chem. 28 (1963) 498-501
15. Milewska M.J., Bytner T., and Polonski T. Synthesis (1996) 1485-1488
16. Yamamoto I., Tabo Y., and Gotoh H. Tetrahedron Lett. 22 (1971) 2295-2296
17. Dominh T., Johnson A.L., Jones J.E., and Senise Jr. P.P. J. Org. Chem. 42 (1977) 4217-4221
18. Grigg R., Gunaratne H.Q.N., and Sridharan V. J. Chem. Soc., Chem. Commun. (1985) 1183-1184
19. Takahashi I., Kawakami T., Hirano E., Yokota H., and Kitajima H. Synlett (1996) 353-355
20. Mori M., Chiba K., and Ban Y. J. Org. Chem. 43 (1978) 1684-1687
21. Larock R.C., Liu C.-L., Lau H.H., and Varaprath S. Tetrahedron Lett. 25 (1984) 4459-4462
22. Kundu N.G., and Khan M.W. Tetrahedron 56 (2000) 4777-4792
23. Pierce J.G., Waller D.L., and Wipf P. J. Org. Chem. 692 (2007) 4618-4629
24. For review, see:. Murphy P.J., and Lee S.E. J. Chem. Soc., Perkin Trans. 1 (1999) 3049-3068 and references cited therein
25. Hajos G., and Nagy I. Curr. Org. Chem. 12 (2008) 39-58 and references cited therein
26. Flitsch W., and Peters H. Tetrahedron Lett. 10 (1969) 1161-1164
27. Flitsch W., Hampel K., and Hohenhorst M. Tetrahedron Lett. 28 (1987) 4395-4396
28. Flitsch W., and Hampel K. Liebigs Ann. Chem. (1988) 387-390
29. Flitsch W., and Langer W. Liebigs Ann. Chem. (1988) 391-395
30. Flitsch W., and Wernsmann P. Tetrahedron Lett. 22 (1981) 719-722
31. Flitsch W., and Schindler S.R. Synthesis (1975) 685-700
32. Flitsch W., and Russkamp. Liebigs Ann. Chem. (1983) 521-528
33. For a review, see:. Maryanoff B.E., and Reitz A.B. Chem. Rev. 89 (1989) 863-927 and references cited therein
34. Gouvers J.-P., Couthon H., and Sturtz G. Eur. J. Org. Chem. (1999) 3489-3493
35. Petter R.C., Banerjee S., and Englard S. J. Org. Chem. 55 (1990) 3088-3097
36. Dartmann M., Flitsch W., Krebs B., Pandl K., and Westfechtel A. Liebigs Ann. Chem. (1988) 695-704
37. Sampson P., Roussis V., Drtina G.J., Koerwitz F.L., and Wiemer D.F. J. Org. Chem. 51 (1986) 2525-2529
38. Han Q., and Wiemer D.F. J. Am. Chem. Soc. 114 (1992) 7692-7697
39. Aitken R.A., Cooper H.R., and Mehrotra A.P. J. Chem. Soc., Perkin Trans. 1 (1996) 475-483
40. Caballero E., Alonso D., Peláez R., Alvarez C., Puebla P., Sanz F., Medarde M., and Tomé F. Tetrahedron Lett. 45 (2004) 1631-1634
41. Bestmann H.J., Moenius T., and Soliman F. Chem. Lett. 15 (1986) 1527-1528
42. See Supplementary data for detailed experimental conditions.
43. For a review, see:. Bhattacharya A.K., and Thyagarajan G. Chem. Rev. 81 (1981) 415-430 and references cited therein
44. Chopard P.A., Clark V.M., Hudson R.F., and Kirby A.J. Tetrahedron 21 (1965) 1961-1970
45. Pace V., Martínez F., Fernández M., Sinisterra J.V., and Alcántara A.R. Org. Lett. 9 (2007) 2661-2664
46. For reviews, see:. Blass B.E. Tetrahedron 58 (2002) 9301-9320
47. Basu B., Das P., and Das S. Curr. Org. Chem. 12 (2008) 141-158
48. Boullet F.T., Villemin D., Ricard M., Moison H., and Foucaud A. Tetrahedron 41 (1985) 1259-1266
49. Hachemi M., Sebova M.P., Toma S., and Villemin D. Phosphorous Sulfur Silicon Relat. Elem. 113 (1996) 131-136
50. For a review, see:. McKillop A., and Young D.W. Synthesis (1979) 401-422
51. McKillop A., and Young D.W. Synthesis (1979) 481-500
52. Smith B.S., and March J. March's Advanced Organic Chemistry, Reactions. 5th ed. Mechanisms and Structure (2001), Wiley-VCH, Weinheim p 1233
53. Stork G., and Danheiser R. J. Org. Chem. 33 (1973) 1775-1776
54. Van Brunt M.P., Ambenge R.O., and Weinreb S.M. J. Org. Chem. 68 (2003) 3323-3326