Cycloaddition reactions of amino-acid derived cross-conjugated trienes: Stereoselective synthesis of novel heterocyclic scaffolds

Heterocycles

Volumn 70, Issue , 2006, Pages 367-388

  Mitasev, Branko ^a   Yan, Bingli ^a   Brummond, Kay M ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947623746     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-06-s(w)36     Document Type: Article

References (52)

1. Nakamura I., and Yamamoto Y. Chem. Rev. 104 (2004) 2127
2. Aubert C., Buisine O., and Malacria M. Chem. Rev. 102 (2002) 813
3. Ojima I., Tzamarioudaki M., Li Z., and Donovan R.J. Chem. Rev. 96 (1996) 635
4. Kobayashi T., Koga Y., and Narasaka K. J. Organomet. Chem. 624 (2001) 73
5. Jeong N., Lee S., and Sung B.K. Organometallics 17 (1998) 3642
6. Wender P.A., Houstedt L.O., Lim J., Love J.A., Williams T.J., and Yoon J.-Y. J. Am. Chem. Soc. 128 (2006) 6302
7. Paik S.-J., Son S.U., and Chung Y.K. Org. Lett. 1 (1999) 2045
8. Cao P., Wang B., and Zhang X. J Am. Chem. Soc. 122 (2000) 6490
9. Brummond K.M., Chen H., Sill P., and You L. J. Am. Chem. Soc. 124 (2002) 15186
10. Brummond K.M., and Mitasev B. Org. Lett. 6 (2004) 2245
11. Brummond K.M., and You L. Tetrahedron 61 (2005) 6180
12. Burke M.D., and Schreiber S.L. Angew. Chem. Int. Ed. Engl. 43 (2004) 46
13. Schreiber S.L. Science 287 (2000) 1964
14. Beeler A.B., Schaus S.E., and Porco Jr. J.A. Curr. Opin. Chem. Biol. 9 (2005) 277
15. Tan D.S. Nat. Chem. Biol. 1 (2005) 74
16. Brummond K.M., Curran D.P., Mitasev B., and Fischer S. J. Org. Chem. 70 (2005) 1745
17. Werner S., Iyer P.S., Fodor M.D., Coleman C.M., Twining L.A., Mitasev B., and Brummond K.M. J. Comb. Chem. 8 (2006) 368
18. Tsuge O., Wada E., and Kanemasa S. Chem. Lett. 239 (1983)
19. Tsuge O., Wada E., and Kanemasa S. Chem. Lett. (1983) 1525
20. Woo S., Squires N., and Fallis A.G. Org. Lett. 1 (1999) 573
21. Woo S., Legoupy S., Parra S., and Fallis A.G. Org. Lett. 1 (1999) 1013
22. Payne A.D., Willis A.C., and Sherburn M.S. J. Am. Chem. Soc. 127 (2005) 12188
23. For example, Fallis' methodology was applied by Schreiber and coworkers to the diversity-oriented synthesis of a library of polycyclic small molecules:. Kwon O., Park S.B., and Schreiber S.L. For other applications of heteroatom containing cross-conjugated trienes, see. J. Am. Chem. Soc. 124 (2002) 13402
24. Spino C., Liu G., Tu N., and Girard S. J. Org. Chem. 59 (1994) 5596
25. Dion A., Dubé P., and Spino C. Org. Lett. 7 (2005) 5601
26. K. M. Brummond, T. O. Painter, D. A. Probst, B. Mitasev, "Rh(l)-Catalyzed Allenic Carbocyclization Reaction Affording 6- and c-Lactams"" Submitted for publication.
27. The structure of 22a was assigned based on an X-ray of a later intermediate, Diels-Alder product (23a).
28. Best yields were obtained when all three reactions were performed without intermediate purification. See experimental section for details.
29. For the unexpected formation of a similar oxazolidinone. Granier T., and Vasella A. Helv. Chim. Acta. 81 (1998) 865
30. Reactions were run until all starting material was consumed. No byproducts were isolated.
31. Reaction was also not observed with the following dienophiles: 2-cyclohexene, 2-cyclopentene, acrolein and methyl-vinyl ketone.
32. Tacconi G., ladarola P., Marinone F., Righetti P.P., and Desimoni G. Tetrahedron 31 (1975) 1179
33. Rudnichenko A.V., Timoshenko V.M., Chernega A.N., Nesterenko A.M., and Shermolovich Y.G. J. Fluorine Chem. 125 (2004) 1351
34. Burdisso M., Desimoni G., Faita G., Righetti P., and Tacconi G. J. Chem. Soc., Perkin Trans. 7 2 (1989) 845
35. 3 to catalyze hetero Diels-Alder reactions, see. Bednarski M., and Danishefsky S. J. Am. Chem. Soc. 105 (1983) 3716
36. Dujardin G., Leconte S., Coutable L., and Brown E. Tetrahedron Lett. 42 (2001) 8849
37. Hughes K.D., Nguyen T.-L.N., Dyckman D., Dulay D., Boyko W.J., and Giuliano R.M. Tetrahedron: Asymmetry 16 (2005) 273
38. Dujardin G., Rossignol S., and Brown E. Synthesis 763 (1998)
39. Wang B., Cao P., and Zhang X. Tetrahedron Lett. 41 (2000) 8041
40. Jolly R.S., Luedtke G., Sheehan D., and Livinghouse T. J. Am. Chem. Soc. 112 (1990) 4965
41. Mandai T., Suzuki S., Ikawa A., Murakami T., Kawada M., and Tsuji J. Tetrahedron Lett. 32 (1991) 7687
42. For Ag(l)-catalyzed cycization of allenic acids, see. Marshall J.A., Wolf M.A., and Wallace E.M. J. Org. Chem. 59 (1994) 7169
43. Baldwin J.E., Thomas R.C., Kruse L.I., and Silberman L. J. Org. Chem. 42 (1977) 3846
44. Lautens M., Fagnou K., and Yang D. J. Am. Chem. Soc. 125 (2003) 14884
45. Recently, a comprehensive study examined the effects contributing to the observed stereochemistry for thermal and Lewis acid catalyzed reactions of relatively unfunctionalized hexadienyl-acrylates. (a) E. L. Pearson, L. C. H. Kwan, C. I. Turner, G. A. Jones, A. C. Willis, M. N. Paddon-Row, and M. S. Sherburn, J. Org. Chem., 2006, 71, 6099. In general, difficulties associated with Diels-Alder reactions of ester-tethered substrates are attributed to existence of the ester moiety in an unfavorable transoid conformation in order to minimize repulsive dipole interactions. For a successful Diels-Alder reaction, the ester needs to rotate into a less favorable cisoid conformation that results in increase of the net dipole moment and steric repulsion between the two alkyl groups. (b) P. Deslongchamps, Stereoelectronic Effects in Organic Chemistry; Pergamon: Oxford, 1983; 54-100. Earlier studies have unveiled a dramatic solvent effect on the ester tethered Diels-Alder reaction. (c) M. E. Jung and J. Gervay, J. Am. Chem. Soc., 1989, 111, 5469.
46. Alexakis A., Jachiet D., and Toupet L. Tetrahedron 45 (1989) 6203
47. Chen C.-Y., and Hart D.J. J. Org. Chem. 58 (1993) 3840
48. 2 catalyzed reaction. Tetrahedron 61 (2005) 7087
49. Saito A., Yanai H., and Taguchi T. Tetrahedron 60 (2004) 12239
50. Highest yield (50%) of the tricyclic lactone (34) was obtained when the reaction was performed at lower concentrations (0.01M), suggesting that side reactions may be responsible for the low yield (mass spectral analysis of the reaction mixture suggested the presence of dimeric products possibly arising from a Diels-Alder reaction of the more reactive diene in the product with an acrylic ester moiety from a molecule of unreacted starting material). Personal communication from Dr. Stefan Werner.
51. Ball G.E., Cullen W.R., Fryzuk M.D., James B.R., and Rettig S.J. Organometallics 10 (1991) 3767
52. Castelhano A.L., Home S., Taylor G.J., Billedeau R., and Krantz A. Tetrahedron 44 (1988) 5451