Total regio- and stereoselective synthesis of perhydropyrrolo[3,4-c]pyrazole derivatives by [3+2] intramolecular dipolar cycloaddition reaction on chiral perhydro-1,3-benzoxazines

Synthesis

Volumn , Issue 9, 2003, Pages 1457-1461

  Pedrosa, Rafael ^a   Andrés, Celia ^a   Maestro, Alicia ^a   Nieto, Javier ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Asymmetric synthesis; Azomethine imines; Dipolar cycloaddition; Pyrazolidines; Stereoselective synthesis

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; ISOMERS; ORGANIC COMPOUNDS; SUBSTITUTION REACTIONS;

DIASTEREOISOMERS;

SYNTHESIS (CHEMICAL);

BENZOXAZINE DERIVATIVE; PYRAZOLE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CHIRALITY; CYCLOADDITION; DIASTEREOISOMER; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 0038236023     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40193     Document Type: Article

References (33)

1. (a) Carruthers, W. In Cycloaddition Reaction in Organic Synthesis, Tretrahedron Organic Chemistry Series, Vol. 8; Pergamon: Oxford, 1990, 269.
2. (b) Padwa, A. In Comprehensive Organic Syhthesis, Vol. 4; Semmelhack, M., Ed.; Pergamon: Oxford, 1991, 1069.
3. (c) Cinquini, M.; Cozzi, F. In Houben-Weyl, Stereoselective Synthesis, E21, Vol. 5; Helmchen, G.; Hoffmann, R. W.; Mulzer, J.; Schaumann, E., Eds.; Thieme Verlag: Stuttgart, 1996, 2953.
4. Confalone, P. N.; Huie, E. M. Org. React. 1988, 36, 1.
5. Kozikowski, A. P. Acc. Chem. Res. 1984, 17, 410.
6. Tsuge, O.; Kanemasa, S. Adv. Heterocycl. Chem. 1989, 45, 231.
7. Grashey, R. In 1,3-Dipolar Cycloaddition Chemistry, Vol. 1; Padwa, A., Ed.; Wiley: New York, 1984, 733.
8. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1963, 2, 565.
9. Shimizu, T.; Hayashi, Y.; Miki, M.; Teramura, K. J. Org. Chem. 1987, 52, 2277.
10. (a) Grigg, R. Chem. Soc. Rev. 1987, 16, 89,
11. (b) Noguchi, M.; Yamada, K. Synthesis 1993, 145.
12. (c) Sun, B.; Adachi, K.; Noguchi, M. Tetrahedron 1996, 52, 901.
13. (d) Sun, B.; Adachi, K.; Noguchi, M. Synthesis 1997, 53,
14. (e) Arrieta, A.; Carrillo, J. R.; Cossío, F. P.; Díaz-Ortiz, A.; Gómez-Escalonilla, M. J.; Hoz, A.; Langa, F.; Moreno, A. Tetrahedron 1998, 54, 13167.
15. (a) Washizuka, K. I.; Nagai, K.; Minakata, S.; Ryu, I.; Konatsu, M. Tetrahedron Lett. 1999, 40, 8849.
16. (b) Washizuka, K. I.; Nagai, K.; Minakata, S.; Ryu, I.; Konatsu, M. Tetrahedron Lett. 2000, 41, 691.
17. Grigg, R.; Heaney, F.; Idle, J.; Somasunderam, A. Tetrahedron Lett. 1990, 31, 2767.
18. (a) Lehman, L. S.; Baclawski, L. M.; Harris, S. A.; Heine, H. W.; Springer, J. P.; VandenHeuvel, W. J. A.; Arison, B. H. J. Org. Chem. 1981, 46, 320.
19. (b) Molchanov, A. P.; Sipkin, D. I.; Koptelov, Y. B.; Kostikov, R. R. Synlett 2000, 1779.
20. (c) Molchanov, A. P.; Sipkin, D. I.; Koptelov, Y. B.; Kostikov, R. R. Eur. J. Org. Chem. 2002, 453.
21. Meier, H.; Heimgartner, H. Helv. Chim. Acta 1986, 69, 927; and references cited therein.
22. (a) Oppolzer, W. Tetrahedron Lett. 1970, 2199.
23. (b) Oppolzer, W. Tetrahedron Lett. 1970, 3091.
24. (c) Jacobi, P. A.; Martinelli, M. J.; Polanc, S. J. Am. Chem. Soc. 1984, 106, 5594.
25. (d) Jungheim, L. N.; Sigmund, S. K. J. Org. Chem. 1987, 52, 4007.
26. (e) Kanemasa, S.; Tomoshige, N.; Wada, E.; Tsuge, O. Bull. Chem. Soc. Jpn. 1989, 62, 3944.
27. (f) Fuchi, N.; Doi, T.; Cao, B.; Kahn, M.; Takahashi, T. Synlett 2002, 285.
28. (g) Fuchi, N.; Doi, T.; Harada, T.; Urba, J.; Cao, B.; Kahn, M.; Takahashi, T. Tetrahedron Lett. 2001, 42, 1305.
29. Wade, P. A. In Comprehensive Organic Synthesis, Vol. 4; Semmelhack, M., Ed.; Pergamon: Oxford, 1991, 1111.
30. Gothelf, K. V.; Jorgensen, K. A. Chem Rev. 1998, 98, 863.
31. Pedrosa, R.; Andrés, C.; Heras, L.; Nieto, J. Org. Lett. 2002, 4, 2513.
32. Condon, F. E. J. Org. Chem. 1972, 37, 3608.
33. Pedrosa, R.; Andrés, C.; Rosón, C. D.; Vicente, M. J. Org. Chem. 2003, 68, 1852.