Conjugate addition of nitroalkanes to N-substituted maleimides. Synthesis of 3-alkylsuccinimides and pyrrolidines

Tetrahedron

Volumn 59, Issue 20, 2003, Pages 3603-3608

  Ballini, Roberto ^a   Bosica, Giovanna ^a   Cioci, Gianluca ^a   Fiorini, Dennis ^a   Petrini, Marino ^a  

^a UNIVERSITY OF CAMERINO   (Italy)

Author keywords

Addition reactions; Imides; Nitro compounds; Pyrrolidines; Reduction

Indexed keywords

ALKENE DERIVATIVE; MALEIMIDE DERIVATIVE; NITROALKENE; PYRROLIDINE DERIVATIVE; SUCCINIMIDE DERIVATIVE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL PROCEDURES; CHEMICAL REACTION; CONJUGATE; HYDROGENATION; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 0037727677     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00508-8     Document Type: Article

References (41)

1. Review (a) Mitchinson A., Nadin A. J. Chem. Soc. Perkin Trans. 1. 2000;2862-2892 (b) Pinchon M., Figadère B. Tetrahedron: Asymmetry. 7:1996;927-964.
2. Review (a) Mitchinson A., Nadin A. J. Chem. Soc. Perkin Trans. 1. 2000;2862-2892 (b) Pinchon M., Figadère B. Tetrahedron: Asymmetry. 7:1996;927-964.
3. For some recent examples see: (a) Verma S.K., Atanes M.N., Busto J.H., Thai D.L., Rapoport H. J. Org. Chem. 67:2002;1314-1318 (b) Schlummer B., Hartwig J.F. Org. Lett. 4:2002;1471-1474 (c) Palacios F., Alonso C., Amezua P., Rubiales G. J. Org. Chem. 67:2002;1941-1946 (d) Smith S.C., Bentley P.D. Tetrahedron Lett. 43:2002;899-902 (e) Karlsson S., Högberg H.-E. Tetrahedron: Asymmetry. 712:2001;1977-1982.
4. For some recent examples see: (a) Verma S.K., Atanes M.N., Busto J.H., Thai D.L., Rapoport H. J. Org. Chem. 67:2002;1314-1318 (b) Schlummer B., Hartwig J.F. Org. Lett. 4:2002;1471-1474 (c) Palacios F., Alonso C., Amezua P., Rubiales G. J. Org. Chem. 67:2002;1941-1946 (d) Smith S.C., Bentley P.D. Tetrahedron Lett. 43:2002;899-902 (e) Karlsson S., Högberg H.-E. Tetrahedron: Asymmetry. 712:2001;1977-1982.
5. For some recent examples see: (a) Verma S.K., Atanes M.N., Busto J.H., Thai D.L., Rapoport H. J. Org. Chem. 67:2002;1314-1318 (b) Schlummer B., Hartwig J.F. Org. Lett. 4:2002;1471-1474 (c) Palacios F., Alonso C., Amezua P., Rubiales G. J. Org. Chem. 67:2002;1941-1946 (d) Smith S.C., Bentley P.D. Tetrahedron Lett. 43:2002;899-902 (e) Karlsson S., Högberg H.-E. Tetrahedron: Asymmetry. 712:2001;1977-1982.
6. For some recent examples see: (a) Verma S.K., Atanes M.N., Busto J.H., Thai D.L., Rapoport H. J. Org. Chem. 67:2002;1314-1318 (b) Schlummer B., Hartwig J.F. Org. Lett. 4:2002;1471-1474 (c) Palacios F., Alonso C., Amezua P., Rubiales G. J. Org. Chem. 67:2002;1941-1946 (d) Smith S.C., Bentley P.D. Tetrahedron Lett. 43:2002;899-902 (e) Karlsson S., Högberg H.-E. Tetrahedron: Asymmetry. 712:2001;1977-1982.
7. For some recent examples see: (a) Verma S.K., Atanes M.N., Busto J.H., Thai D.L., Rapoport H. J. Org. Chem. 67:2002;1314-1318 (b) Schlummer B., Hartwig J.F. Org. Lett. 4:2002;1471-1474 (c) Palacios F., Alonso C., Amezua P., Rubiales G. J. Org. Chem. 67:2002;1941-1946 (d) Smith S.C., Bentley P.D. Tetrahedron Lett. 43:2002;899-902 (e) Karlsson S., Högberg H.-E. Tetrahedron: Asymmetry. 712:2001;1977-1982.
8. (a) Krow G.R., Yuan J., Lin G., Sonnet P.E. Org. Lett. 4:2002;1259-1262
9. (b) Greenwood E.S., Parsons P.J. Synlett. 2002;167-169
10. (c) Li Z., Feiten H.-J.-, Chang D., Duetz W.A., van Beilen J.B., Witholt B. J. Org. Chem. 66:2001;8424-8430.
11. Reviews: (a) Speckamp W.N., Moolenaar M.J. Tetrahedron. 56:2000;3817-3856 (b) De Koning H., Speckamp W.N. Helmchen G., Hoffman R.W., Mulzer J., Schaumann E. Stereoselective Synthesis (Houben-Weyl). Vol. E21:1995;1953-2009 Georg Thieme, Stuttgart.
12. Reviews: (a) Speckamp W.N., Moolenaar M.J. Tetrahedron. 56:2000;3817-3856 (b) De Koning H., Speckamp W.N. Helmchen G., Hoffman R.W., Mulzer J., Schaumann E. Stereoselective Synthesis (Houben-Weyl). Vol. E21:1995;1953-2009 Georg Thieme, Stuttgart.
13. (a) Enders D., Teschner P., Raabe G., Runsink J. Eur. J. Org. Chem. 2001;4463-4477
14. (b) Zhang X., Jang W., Schmitt A.C. Tetrahedron Lett. 42:2001;4943-4945
15. (c) Hitchcock P.B., Starkmann B.A., Young D.W. Tetrahedron Lett. 42:2001;2381-2384
16. (d) Cossy J., Tresnard L., Belotti D., Gomez Pardo D. Tetrahedron Lett. 42:2001;251-254.
17. Chihab-Eddine A., Daïch A., Jilale A., Decroix B. Tetrahedron Lett. 42:2001;573-576.
18. (a) Curran D.P., Geib S., De Mello N. Tetrahedron. 55:1999;5681-5704
19. (b) Mikami T., Harada M., Narasaka K. Chem. Lett. 1999;425-426
20. (c) Gutemberger G., Steckhan E., Blechert S. Angew. Chem. Int. Ed. 37:1998;660-662
21. (d) Meggers E., Steckhan E., Blechert S. Angew. Chem. Int. Ed. 34:1995;2137-2139.
22. Cunningham I.D., Brownhill A., Hamerton I., Howlin B. Tetrahedron. 53:1997;13473-13494.
23. (a) Ono N. The Nitro Group in Organic Synthesis. 2001;Wiley-VCH, New York,
24. (b) Perlmutter P. Conjugate Addition Reactions in Organic Synthesis. 1992;Pergamon, Oxford.
25. (a) Ballini R., Bosica G., Tetrahedron 1995;51;4213-4222
26. (b) Ballini R., Bosica G. Liebigs Ann. 1996;2087-2089.
27. Ballini R., Barboni L., Bosica G., Petrini M. Synlett. 2000;391-393.
28. Ballini R., Bosica G., Fiorini D., Giarlo G. Synthesis. 2001;2003-2006.
29. Ballini R., Bosica G., Fiorini D., Gil M.V., Petrini M. Org. Lett. 3:2001;1265-1267.
30. Ballini R., Bosica Masè A., Petrini M. Eur. J. Org. Chem. 2000;2927-2931.
31. Katritzky A.R., Yao J., Qi M., Chou Y., Sikora D.J., Davis S. Hetrocycles. 48:1998;2677-2691.
32. (a) Ballini R., Bosica G. Synlett. 1996;1115-1116.
33. For a review on this reducing couple see: (b) Ganem B., Osby J.O. Chem. Rev. 86:1986;763-780.
34. (a) Tsuzuki Y., Chiba K., Hino K. Tetrahedron: Asymmetry. 12:2001;1793-1799
35. (b) Zhang H.K., Chen Q.F., Huang P.Q. Synth. Commun. 30:2000;2431-2444
36. (c) Rao V.D., Perisamy M. Synthesis. 2000;703-706
37. (d) Kuwano R., Takahashi M., Ito Y. Tetrahedron Lett. 39:1998;1017-1020
38. (e) Marson C.M., Melling R.C. Chem. Commun. 1998;1223-1224
39. (f) Macor J., Blank D.H., Ryan K., Post R.J. Synthesis. 1997;443-449.
40. Abramovitch R.A., Chapman A.V. Heterocycles. 40:1995;89-92.
41. Beugelmans R., Benadjila-Iguertsira L., Chastanet J., Negron G., Roussi G. Can. J. Chem. 63:1985;725-734.