The use of nonactivated iminodienophiles in the stereoselective aza-Diels-Alder reaction

Tetrahedron Asymmetry

Volumn 15, Issue 3, 2004, Pages 445-452

  Trifonova, Anna ^a   Andersson, Pher G ^a  

^a UPPSALA UNIVERSITY   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ALANINE; ALDEHYDE; AMINO ACID; CYCLOPENTADIENE DERIVATIVE; HETEROCYCLIC COMPOUND; IMINE; LACTIC ACID; LEWIS ACID; NITROGEN; PHTHALIMIDE;

AMINO ACID SYNTHESIS; ARTICLE; CHIRALITY; CYCLOADDITION; DESS MARTIN OXIDATION; DIELS ALDER REACTION; ENANTIOMER; ENANTIOSELECTIVITY; PRIORITY JOURNAL; RACEMIZATION; STEREOCHEMISTRY;

EID: 0742306893     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2003.12.011     Document Type: Article

References (45)

1. Hetero Diels-Alder Methodology in Organic Synthesis; Academic: London, 1987; Chapter 2.
2. Alonso D.A., Guijarro D., Pinho P., Temme O., Andersson P.G. J. Org. Chem. 63:1998;2749.
3. Södergren M.J., Bertilsson S.K., Andersson P.G. J. Am. Chem. Soc. 122:2000;6610.
4. Brandt P., Andersson P.G. Synlett. 2000;1092.
5. Murata K., Ikariya T., Noyori R. J. Org. Chem. 64:1999;2186.
6. O'Brien P. J. Chem. Soc., Perkin Trans. 1. 1998;1439.
7. de Sousa S.E., O'Brien P., Steffens H.C. Tetrahedron Lett. 40:1999;8423.
8. Stella L., Abraham H., Feneau-Dupont J., Tinant B., Declercq J.P. Tetrahedron Lett. 31:1990;2603.
9. Abraham H., Stella L. Tetrahedron. 48:1992;9707.
10. Waldmann H., Braun M. Liebigs Ann. Chem. 1991;1045.
11. Bailey P.D., Brown G.R., Korber F., Reed A., Wilson R.D. Tetrahedron: Asymmetry. 2:1991;1263.
12. Bailey P.D., Wilson R.D., Brown G.R. J. Chem. Soc., Perkin Trans. 1. 1991;1337.
13. Jörgensen K.A. Angew. Chem., Int. Ed. 39:2000;3558.
14. Fringuelli F., Piermatti O., Pizzo F., Vaccaro L. Eur. J. Org. Chem. 2001;439.
15. Buonora P., Olsen J.-C., Oh T. Tetrahedron. 57:2001;6099.
16. Herczegh P., Kovacs I., Szilagyi L., Zsely M., Sztaricskai F., Berecibar A., Olesker A., Lukacs G. Tetrahedron Lett. 33:1992;3133.
17. Herczegh P., Kovacs I., Szilagyi L., Sztaricskai F. Tetrahedron. 50:1994;13671.
18. Herczegh P., Kovacs I., Erdösi G., Varga T., Agocs A., Szilagyi L., Sztaricskai F., Berecibar A., Lukacs G., Olesker A. Pure Appl. Chem. 69:1997;519.
19. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., Galvez J.A. Tetrahedron Lett. 38:1997;2547.
20. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., Galvez J.A. Tetrahedron. 55:1999;7601.
21. Vacca J.P. Tetrahedron Lett. 26:1985;1277.
22. Badorrey R., Cativiela C., Diaz-de-Villegas M.D., Galvez J.A. Tetrahedron. 58:2002;341.
23. Avenoza A., Busto J.H., Cativiela C., Corzana F., Peregrina J.M., Zurbano M.M. J. Org. Chem. 67:2002;598.
24. Midland M.M., McLoughlin J.I. Tetrahedron Lett. 29:1988;4653.
25. Midland M.M., Koops R.W. J. Org. Chem. 57:1992;1158.
26. Ishimaru K., Yamomoto Y., Akiba K.-j. Tetrahedron. 53:1997;5423.
27. Danishefsky S., Langer M.E., Vogel C. Tetrahedron Lett. 26:1985;6983.
28. Yu L., Li J., Ramirez J., Chen D., Wang P.G. J. Org. Chem. 62:1997;903.
29. Takai K., Heathcock C.H. J. Org. Chem. 50:1985;3247.
30. 12 into desired aldehyde.
31. Mancuso A.J., Huang S.-L., Swern D. J. Org. Chem. 43:1978;2480.
32. Chu S.H., Chen Z.H., Weng Z.Y., Rowe E.C., Chu E., Chu M.-Y.W. J. Heterocyclic Chem. 24:1987;989.
33. Alvarez M., Fernandez D., Joule J.A. Tetrahedron Lett. 42:2001;315.
34. 12 furnished compound 4 in 80% yield.
35. Nagao Y., Dai W.-M., Ochiai M., Shiro M. Tetrahedron. 46:1990;6361.
36. Carocci A., Catalano A., Corbo F., Duranti A., Amoroso R., Franchini C., Lentini G., Tortorella V. Tetrahedron: Asymmetry. 11:2000;3619.
37. Dess D.B., Martin J.C. J. Org. Chem. 48:1983;4156.
38. Dess D.B., Martin J.C. J. Am. Chem. Soc. 113:1991;7277.
39. Balenovic K., Bregant N., Cerar D., Files D., Jambresic I. J. Org. Chem. 18:1953;297.
40. Gacek M., Undheim K. Tetrahedron. 30:1974;4233.
41. Becker Y., Eisenstadt A., Stille J.K. J. Org. Chem. 45:1980;2145.
42. Williams H.W.R., Rooney C.S. Synth. Commun. 7:1977;201.
43. Green I.M., Delpierre G.R. S. Afr. J. Chem. 30:1977;183.
44. Palomo C., Cossio F.P., Cuevas C., Lecea B., Mielgo A., Roman P., Luque A., Martinez-Ripoll M. J. Am. Chem. Soc. 114:1992;9360.
45. Kurihara K., Sugimoto T., Saitoh Y., Igarashi Y., Hirota H., Moriyama Y., Tsuyuki T., Takahashi T., Khuong-Huu Q. Bull. Chem. Soc. Jpn. 58:1985;3337.