[4+2] Annulatlon - Convenient synthesis of substituted dihydropyranones in aqueous media

European Journal of Organic Chemistry

Volumn , Issue 12, 2009, Pages 2003-2009

  Ouyang, Yan ^a,c   Huang, Jie ^a,b   Pan, Wei ^a   Liang, Yongjiu ^b   Yang, Yang ^a   Dong, Dewen ^a,b  

^a NORTHEAST NORMAL UNIVERSITY   (China)

^b CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^c Yili Normal University   (China)

Author keywords

oxo ketene S,S acetals; Aldol reactions; Annulation; Dihydropyranones; Water

Indexed keywords

EID: 63849248236     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801257     Document Type: Article

References (61)

1. a) D. L, Boger, S. H. Weinreb Hetero-Diels-Alder Methodology ill Organic Synthesis academic Press, New York, 1987:
2. H. B. Kagan Comprehensive Organic Chemistry: Pergamon, Oxford. 1992, vol. 8;
3. nd ed.. Prentice Hall. Upper Saddle River, NJ, 1996:
4. K.C. Nicolaou, E. J. Sorensen, Classics in Total Synthesis Wiley-VCH. Weinheim, 1996:
5. R. Noyori, Asymmetric Catalysis in Organic Synthesis, Wiley, New York. 1994.
6. a) S. J. Danishefsky, Aldrichim. Acta 1986. 19, 59-68:
7. R. R. Schmidt, Acc. Chem. Res. 1986, 19, 250-259:
8. T. L. B. Boivin. Tetrahedron 1987, 43, 3309-3362;
9. W. Oppolzer, I. Rodriguez. Helv. Chim. Acta 1993, 76, 1275-1281;
10. S.J. Danishefsky. M. T. Bilodeau. Angew. Chem. Int. Ed. Engl. 1996, 35, 1380-1419;
11. E. J. Corey. A. Guzman-Perez, Angew. Chem.. Int. Ed. 1998, 37, 388-401;
12. L. F. Tietze, Curr. Org. Chem. 1998, 2, 19-62;
13. K. A. Jørgensen. Angew. Chem. Int. Ed. 2000, 39, 3558-3588.
14. a) S. J. Danishefsky, W. H. Pearson, B. E. Segmuller, J. Am. Chem. Soc. 1985. 107, 1280-1285;
15. S. J. Danishefsky, M. P. DeNinno, Angew. Chem. Int. Ed. Engl. 1987, 26, 15-23.
16. M. Reiter, S. Ropp, V. Gouverneur, Org Lett. 2004, 6, 91-94.
17. a) J. D. Rainier. S. P. Allwein, J. M. Cox. Org. Lett. 2000, 2, 231-234;
18. J. M. Cox, J. D. Rainier, Org. Lett. 2001, 3,2919-2922;
19. Y. Yamashita, S. Saito. H. Ishitani. S. Kobayashi, J. Am. Chem.. Soc. 2003, 125, 3793-3798.
20. a) S. J. Danishefsky, J. F. Kerwin, S. Kobayashi, J. Am. Chem. Soc. 1982. 104, 358-360:
21. S. J. Danishefsky, J. F. Kerwin, J. Org. Chem. 1982, 47, 3183-3184.
22. a) S. J. Danishefsky, E. Larson, D. Askin, N. Kato, J. Am. Chem. Soc. 1985, 107, 1246-1255;
23. S. J.Danishefsky, C.J. Maring, J. Am. Chem. Soc. 1985, 107, 1269-1274;
24. S. J. Danishefsky, D. C. Myles, D. F. Harvey, J. Am. Chem. Soc. 1987, 109, 862-867;
25. S. J. Danishefsky, S. DeNinno, P. Lartey, J. Am. Chem. Soc. 1987, 109, 2082-2089;
26. S. J. Gould, R. L. Eisenburg, L. R. Hillis, Tetrahedron 1991, 47, 7209-7218;
27. R. Anminziata, M. Cinquini, F. Cozzi, P. G. Cozzi, L. Raimondi, J. Org. Chem. 1992, 57, 3605-3609;
28. M. T. Reetz, G. Gansäuer, Tetrahedron 1993, 49, 6025-6030;
29. G. Yang, D. C. Myles, Tetrahedron Lett. 1994, 35, 2503-2504;
30. M. T. Burger, W. C. Still, J. Org. Chem. 1996, 61, 775-777;
31. P. A. Evans, J. D. Nelson, J. Org. Chem. 1996, 61, 7600-7602;
32. W. Yang, D. Shang, Y. Liu, Y. Du, X. Feng, J. Org. Chem. 2005, 70, 8533-8537.
33. a) M. Bednarski, C. Maring, S. Danishefsky, Tetrahedron Lett. 1983, 24, 3451-3454:
34. K. Maruoka, T. Itoh, T. Shirasaka, H. Yamamoto, J. Am. Chem. Soc. 1988, 110, 310-312;
35. Q. Gao, T. Marayama, M. Mouri. H. Yamamoto, J. Org. Chem. 1992, 57, 1951-1952;
36. E. J. Corey, C. L. Cywin, T. D. Roper, Tetrahedron Lett. 1992, 33, 6907-6910:
37. Q. Gao, K. Ishihara, T. Maruyama, M. Mouri, H. Yamamoto, Tetrahedron 1994, 50, 979-988;
38. K. Mikami, O. Kotera, Y. Motoyama, H. Sakaguchi, Synlett 1995, 975-977;
39. G. E. Keck, X.-Y. Li, D. Krishnainurthy, J. Org. Chem. 1995, 60, 5998-5999;
40. H. Du, J. Long, J. Hu. X. Li, K. Ding, Org. Lett. 2002, 4, 4349-4352.
41. a) X.-F. Yang, J. F. Mague, C.-J. Li, J. Org. Chem. 2001, 66, 739-747;
42. b) J.S. Yadav, B. V. Subba Reddy, G. Mahesh Kumar, Ch. V. S. R. Murthy, Tetrahedron Lett. 2001, 42, 89-91;
43. S. Marumoto. J. J. Jaber, J. P. Vitale, S. D. Rychnovsky, Org. Lett. 2002, 4, 3919-3922;
44. S. Gelin, R. Gelin. Bull. Soc. Chim. Fr. 1969, 4091-4102.
45. J. D. Winkler, K. Oh, Org. Lett. 2005, 7, 2421-2423.
46. D.W. Jeffery, M. V. Perkins. J. M. White. Org. Lett. 2005, 7, 407-409.
47. a) B. Gao, Z. Yu, Z. Fu, X. Feng, Tetrahedron Lett. 2006, 47, 1537-1539;
48. D. S. Matteson, H.-W. Man, O. C. Ho, J. Am. Chem. Soc. 1996, 118, 4560-4566.
49. For reviews, see: a) R. K. Dieter, Tetrahedron 1986, 42, 3029-3096;
50. Y. Tominaga, J. Heterocycl. Chem. 1989, 26,1167-1204;
51. H. Junjappa, II. Ha, C. V. Asokan, Tetrahedron 1990, 46, 5423-5506;
52. M. Kolb, Synthesis 1990, 171-190.
53. a) X. Bi, D. Dong, Q. Liu, W. Pan, L. Zhao, B. Li, J. Am. Chem. Soc. 2005, 127, 4578-4579;
54. D. Dong, X. Bi, Q. Liu, F. Cong, Chem. Commun. 2005, 3580-3582;
55. X. Bi, D. Dong, Y Li, Q. Liu, Q. Zhang, J. Org. Chem. 2005, 70, 10886-10889.
56. Y. Ouyang, D. Dong, W. Pan, J. Zhang, Q. Liu, Tetrahedron 2006,62,10111-10116.
57. W. Pan. D. Dong, Y. Ouyang, R. Wu, Y. Yang, Q. Liu, Synthesis 2007, 2115-2120.
58. Y. Ouyang, D. Dong, H. Yu, Y Liang, Q. Liu, Adv. Synth. Catal. 2006, 348, 206-210.
59. a) C. F. Bernasconi, D. F. Sclruck, R. J. Ketner, I. Eventova, Z. Rappoport, J. Am. Chem. Soc. 1995, 117, 2719-2725;
60. C. F. Bernasconi, Tetrahedron 1989, 45, 4017-4090;
61. C. F. Bernasconi, R. J. Ketner, X. Chen, Z. Rappoport, J. Am. Chem. Soc. 1998, 120, 7461-7468.