Regioselective Rh-catalyzed Allylic Amination/Ring-closing Metathesis Approach to Monocyclic Azacycles: Diastereospecific Construction of 2,5-disubstituted Pyrrolines

Organic Letters

Volumn 1, Issue 12, 1999, Pages 1929-1931

  Evans, P Andrew ^a   Robinson, John E ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; PYRROLE DERIVATIVE; RHODIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; STEREOISOMERISM;

AMINATION; AZA COMPOUNDS; CATALYSIS; PYRROLES; RHODIUM; STEREOISOMERISM;

EID: 0033576429     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol991064l     Document Type: Article

References (33)

1. For a recent review of methods for constructing saturated nitrogen heterocycles, see: Nadin, A. J. Chem. Soc., Perkin Trans. 1 1998, 3493.
2. For recent examples of general azacycle construction, see: (a) Barluenga, J.; Tomás, M.; Ballesteros, A.; Santamaría, J.; Suárez-Sobrino, A. J. Org. Chem. 1997, 62, 9229.
3. (b) Arredondo, V. M.; McDonald, F. E.; Marks, T. J. J. Am. Chem. Soc. 1998, 120, 4871.
4. (c) Meguro, M.; Yamamoto, Y. Tetrahedron Lett. 1998, 39, 5421.
5. (d) Larock, R. C.; Ty, C.; Pace, P. J. Org. Chem. 1998, 63, 6859.
6. (e) Serino, C.; Stehle, N.; Park, Y. S.; Florio, S,; Beak, P. J. Org. Chem. 1999, 64, 1160.
7. (f) Naito, T.; Nakagawa, K.; Nakamura, T.; Kasei, A.; Ninomiya, I.; Kiguchi, T. J. Org. Chem. 1999, 64, 2003 and pertinent references therein.
8. (a) Evans, P. A.; Nelson, J. D. Tetrahedron Lett. 1998, 39, 1725.
9. (b) Evans, P. A.; Nelson, J. D. J. Am. Chem. Soc. 1998, 120, 5581.
10. Evans, P. A.; Robinson, J. E.; Nelson, J. D. J. Am. Chem. Soc. 1999, 121, 6761.
11. For a recent review on allylic amination, see: Johannsen, M.; Jørgensen, K. A. Chem. Rev. 1998, 98, 1689 and pertinent references therein.
12. For recent reviews on ring-closing metathesis, see: (a) Randall, M. L.; Snapper, M. L. J. Mol. Catal. A: Chem. 1998, 133, 29.
13. (b) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371.
14. (c) Grubbs, R. H. Tetrahedron 1998, 54, 4413.
15. (d) Pandit, U. K.; Overleeft, H. S.; Borer, B. C.; Bieraugel, H. Eur. J. Org. Chem. 1999, 9.
16. For recent approaches to nitrogen heterocycles using ring-closing metathesis, see: (a) Fu, G. C,; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324.
17. (b) Overleeft, H. S.; Bruggeman, P.; Pandit, U. K. Tetrahedron Lett. 1998, 39, 3869.
18. (c) White, J. D.; Hrnciar, P.; Yokochi, A. F. T. J. Am. Chem. Soc. 1998, 120, 7359.
19. (d) Veerman, J. J. N.; Maarseveen, J. H.; Visser, G. M.; Kruse, C. G.; Schoemaker, H. E.; Hiemstra, H.; Rutjes, F. P. J. T. Eur. J. Org. Chem. 1998, 3.
20. (e) Kozmin, S. A.; Rawal, V. H. J. Am. Chem. Soc. 1998, 120, 13523.
21. (f) Pernerstorfer, J.; Schuster, M.; Blechert, S. Synthesis 1999, 138.
22. (g) Tanner, D.; Hagberg, L.; Poulsen, A. Tetrahedron 1999, 55, 1427.
23. (h) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J. Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791.
24. (i) Martin, S. F.; Humphrey, J. M.; Ali, A.; Hillier, M. C. J. Am. Chem. Soc. 1999, 121, 866.
25. (j) Tarling, C. A.; Holmes, A. B.; Markwell, R. E.; Pearson, N. D. J. Chem. Soc., Perkin Trans. 1 1999, 1695.
26. (k) Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron 1999, 55, 8189.
27. (l) Jo, E.; Na, Y.; Chang, S. Tetrahedron Lett. 1999, 40, 5581.
28. (m) Paquette, L. A.; Leit, S. M. J. Am. Chem. Soc. 1999, 121, 8126 and pertinent references cited therein.
29. For recent examples of 2,5-disubstituted pyrrolidine construction, see: (a) Dhimane, H.; Vanucci-Bacqué, C.; Hamon, L.; Lhommet, G. Eur. J. Org. Chem. 1998, 1955.
30. (b) Kawanami, Y.; Iizuna, N.; Okano, K. Chem. Lett. 1998, 1231.
31. (c) Senboku, H.; Hasegawa, H.; Orito, K. Tokuda, M. Heterocycles 1999, 50, 333.
32. (d) Grigg, R.; Thornton-Pett, M.; Yoganathan, G. Tetrahedron 1999, 55, 1763.
33. (e) Katritzky, A. R.; Cui, X.-L. Yang, B. Steel, P. J. J. Org. Chem. 1999, 64, 1979 and pertinent references therein.