Evaluation of ethyl 2-carbomethoxyethenesulfinates as 2-hydroxymethyl enethiol equivalents in the Diels-Alder reaction

Tetrahedron

Volumn 61, Issue 5, 2005, Pages 1115-1125

  Faragher, Robert J ^a   Alberico, Dino ^a   Schwan, Adrian L ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Diels Alder cycloadditions; Lewis acid; Reduction; Stereospecific; Sulfinate

Indexed keywords

LEWIS ACID;

ANALYTIC METHOD; ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DIELS ALDER REACTION; EVALUATION; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; THERMAL ANALYSIS;

BETULACEAE;

EID: 12344308233     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.11.050     Document Type: Article

References (58)

1. M.C. Carreno Chem. Rev. 95 1995 1717 1760
2. O. De Lucchi, and L. Pasquato Tetrahedron 44 1988 6755 6794
3. I. Forrestal, and C.M. Rayner C.M. Rayner Advances in Sulfur Chemistry Vol. 2 2000 JAI Stanford 185 195
4. A.W.M. Lee, W.H. Chan, H.K. Zhang, and P.F. Xia Curr. Org. Chem. 7 2003 573 583
5. A.M. Harned, S. Mukherjee, D.L. Flynn, and P.R. Hanson Org. Lett. 5 2003 15 18
6. V.O. Rogatchov, H. Bernsmann, P. Schwab, R. Frohlich, B. Wibbeling, and P. Metz Tetrahedron Lett. 43 2002 4753 4756
7. B. Plietker, D. Seng, R. Frohlich, and P. Metz Tetrahedron 56 2000 873 879
8. H. Bernsmann, R. Frohlich, and P. Metz Tetrahedron Lett. 41 2000 4347 4351
9. H. Bernsmann, B. Hungerhoff, R. Fechner, R. Frohlich, and P. Metz Tetrahedron Lett. 41 2000 1721 1724
10. U. Meiners, E. Cramer, R. Froehlich, B. Wibbeling, and P. Metz Eur. J. Org. Chem. 1998 2073 2078
11. P. Metz, D. Seng, R. Froehlich, and B. Wibbeling Synlett 1996 741 742
12. P. Metz, U. Meiners, E. Cramer, R. Froehlich, and B. Wibbeling Chem. Commun. 1996 431 432
13. P. Metz, M. Fleischer, and R. Frohlich Tetrahedron 51 1995 711 732
14. P. Metz, J. Stoelting, M. Luege, and B. Krebs Angew. Chem., Int. Ed. Engl. 33 1994 2195 2197
15. E. Cramer, M. Fleischer, U. Meiners, J. Stoelting, and P. Metz Phosphorus, Sulfur Silicon Relat. Elem. 95-96 1994 487 488
16. P. Metz, and E. Cramer Tetrahedron Lett. 34 1993 6371 6374
17. P. Metz, and M. Fleischer Synlett 1993 399 400
18. P. Metz, M. Fleischer, and R. Froehlich Synlett 1992 985 987
19. E. Bovenschulte, P. Metz, and G. Henkel Angew. Chem., Int. Ed. Engl. 28 1989 202 204
20. K.F. Ho, D.C.W. Fung, W.Y. Wong, W.H. Chan, and A.W.M. Lee Tetrahedron Lett. 42 2001 3121 3124
21. L.S. Jiang, W.H. Chan, and A.W.M. Lee Tetrahedron 55 1999 2245 2262
22. A.W.M. Lee, W.H. Chan, Z.P. Zhong, K.F. Lee, and A.B.W. Yeung J. Chem. Res., (S) 1998 326 327
23. A.W.M. Lee, W.H. Chan, L.S. Jiang, and K.W. Poon Chem. Commun. 1997 611 612
24. W.H. Chan, A.W.M. Lee, L.S. Jiang, and T.C.W. Mak Tetrahedron: Asymmetry 8 1997 2501 2504
25. A. Waldner Tetrahedron Lett. 30 1989 3061 3064
26. E.D. Weiler, and J.J. Brennan J. Heterocycl. Chem. 15 1978 1299 1302
27. A.S. Bell, C.W.G. Fishwick, and J.E. Reed Tetrahedron 55 1999 12313 12330
28. W.H. Chan, A.W.M. Lee, and K.M. Lee J. Chem. Res., (S) 1994 138 139
29. A.L. Schwan, J.L. Snelgrove, M.L. Kalin, R.D.J. Froese, and K. Morokuma Org. Lett. 1 1999 487 489
30. Y. Lear, and A.L. Schwan J. Org. Chem. 64 1999 8138 8143
31. Y. Vallee, M. Khalid, J.L. Ripoll, and A. Hakiki Synth. Commun. 23 1993 1267 1271
32. M. Ochiai, S. Yamamoto, T. Suefuji, and D.-W. Chen Org. Lett. 3 2001 2753 2756
33. A.M. Le Nocher, and P. Metzner Tetrahedron Lett. 33 1992 6151 6154
34. B.F. Bonini, M. Comes-Franchini, M. Fochi, G. Mazzanti, and A. Ricci Tetrahedron 52 1996 4803 4816
35. C.O. Kappe, S.S. Murphree, and A. Padwa Tetrahedron 53 1997 14179 14233
36. Y. Chung, B.F. Duerr, T.A. McKelvey, P. Nanjappan, and A.W. Czarnik J. Org. Chem. 54 1989 1018 1032
37. R.L. Jarvest, and S.A. Readshaw Synthesis 1992 962 965
38. J. Leroy, H. Molines, and C. Wakselman J. Org. Chem. 52 1987 290 292
39. H. Takayama, A. Iyobe, and T. Koizumi J. Chem. Soc., Chem. Commun. 1986 771 772
40. L.L. Klein, and T.M. Deeb Tetrahedron Lett. 26 1985 3935 3938
41. C.K. McClure, and K.B. Hansen Tetrahedron Lett. 37 1996 2149 2152
42. D.P. Dolata, and R. Bergman Tetrahedron Lett. 28 1987 707 708
43. M.J.S. Dewar, and A.B. Pierini J. Am. Chem. Soc. 106 1984 203 208
44. T.M. Balthazor, B. Gaede, D.E. Korte, and H.S. Shieh J. Org. Chem. 49 1984 4547 4549
45. J.I. Garcia, J.A. Mayoral, and L. Salvatella Acc. Chem. Res. 33 2000 658 664
46. S.M. Bachrach J. Org. Chem. 60 1995 4395 4398
47. F. Yuste, B. Ortiz, J. Israel Perez, A. Rodriguez-Hernandez, R. Sanchez-Obregon, F. Walls, and J.L. Garcia Ruano Tetrahedron 58 2002 2613 2620
48. C.W. Perkins, S.R. Wilson, and J.C. Martin J. Am. Chem. Soc. 107 1985 3209 3218
49. G. Hanson, and D.S. Kemp J. Org. Chem. 46 1981 5441 5443
50. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions Mechanisms and Structure 5th ed. 2001 Wiley-Interscience New York p 1198
51. J.L. Suschitzky J. Chem. Soc., Chem. Commun. 1984 275 276
52. M.D. Brown, and G.H. Whitham J. Chem. Soc., Perkin Trans. 1 1988 817 821
53. W.J. Chen, D.Y. Lee, and R.N. Armstrong J. Org. Chem. 51 1986 2848 2850
54. L. Chacon-Garcia, S. Lagunas-Rivera, S. Perez-Estrada, M.E. Vargas-Diaz, P. Joseph-Nathan, J. Tamariz, and L.G. Zepeda Tetrahedron Lett. 45 2004 2141 2145
55. F. Martinez-Ramos, M.E. Vargas-Diaz, L. Chacon-Garcia, J. Tamariz, P. Joseph-Nathan, and L.G. Zepeda Tetrahedron: Asymmetry 12 2001 3095 3103
56. M. Node, K. Nishide, Y. Shigeta, H. Shiraki, and K. Obata J. Am. Chem. Soc. 122 2000 1927 1936
57. M. Ozeki, K. Nishide, F. Teraoka, and M. Node Tetrahedron: Asymmetry 15 2004 895 907
58. A. Solladie-Cavallo, M. Balaz, M. Salisova, and R. Welter J. Org. Chem. 68 2003 6619 6626