A simple stereoselective synthesis of enantiopure 2-substituted pyrrolidines and piperidines from chiral (R)-phenylglycinol-derived bicyclic 1,3-oxazolidines

European Journal of Organic Chemistry

Volumn , Issue 9, 2000, Pages 1719-1726

  Andrés, José M ^a   Herráiz Sierra, Ignacio ^a   Pedrosa, Rafael ^a   Pérez Encabo, Alfonso ^a  

^a UNIVERSITY OF VALLADOLID   (Spain)

Author keywords

Asymmetric synthesis; Heterocycles; Nitrogen heterocycles; Piperidines; Pyrrolidines

Indexed keywords

HETEROCYCLIC COMPOUND; NITROGEN DERIVATIVE; OXAZOLIDINE DERIVATIVE; PIPERIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; POLYMERIZATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0042865048     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1099-0690(200005)2000:9<1719::aid-ejoc1719>3.0.co;2-r     Document Type: Article

References (39)

1. A. D. Elbein, R. Molyneux, in Alkaloids; Chemical and Biological Perspectives (Ed.: S. W. Pelletier), J. Wiley and Sons, New York, 1987, vol. 57.
2. [2a] C. Andrés, J. P. Duque-Soladana, R. Pedrosa, J. Org. Chem. 1999, 64, 4282-4288.
3. [2b] C. Andrés, J. P. Duque-Soladana, R. Pedrosa, J. Org. Chem. 1999, 64, 4273-4281.
4. [2c] C. Andrés, J. P. Duque-Soladana, J. M. Iglesias, R. Pedrosa, Tetrahedron Lett. 1996, 50, 9085-9086. -
5. [2d] M. García-Valverde, R. Pedrosa, M. Vicente, Tetrahedron 1996, 52, 10761-10770.
6. [3a] C. Scolastico, Pure and Appl. Chem. 1998, 60, 1689.
7. [3b] R. Pedrosa, in Enantioselective Synthesis of β-Amino Acids (Ed.: E. Juaristi), Wiley-VCH, New York, 1996, chap. 17, p. 391.
8. C. Agami, F. Couty, H. Lam, H. Mathieu, Tetrahedron 1998, 54, 8783-8796.
9. C. Agami, F. Couty, O. Vernier, L. Hamon, J. Org. Chem. 1997, 62, 2106-2112.
10. H. Poerwono, K. Higashiyama, H. Takahashi, J. Org. Chem. 1998, 63, 2711-2714.
11. [7a] S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1999, 40, 141-142.
12. [7b] S. M. Allin, C. J. Northfield, M. I. Page, A. M. Z. Slawin, Tetrahedron Lett. 1999, 40, 143-146.
13. E. Bouron, G. Goussard, C. Marchand, M. Bonin, X. Panncoulke, J.-C. Quirion, H. P. Husson, Tetrahedron Lett. 1999, 40, 7227-7230.
14. A. R. Katritzky, X.-L. Cui, B. Yang, P. J. Steel, Tetrahedron Lett. 1998, 39, 1697-1700.
15. A. R. Katritzky, G. Qiu, B. Yang, P. J. Steel, J. Org. Chem. 1998, 63, 6699-6703.
16. C. Maury, Q. Wang, T. Gharbaoui, M. Chiadmi, A. Tomas, J. Royer, H.-P. Husson, Tetrahedron 1997, 53, 3627-3636.
17. A. I. Meyers, L. E. Burgess, J. Org. Chem. 1991, 56, 2294-2296.
18. [13a] M. J. Munchhof, A. I. Meyers, J. Am. Chem. Soc. 1995, 117, 5399-5400.
19. [13b] M. J. Munchhof, A. I. Meyers, J. Org. Chem. 1995, 60, 7084-7085.
20. [13c] M. Amat, N. Llor, J. Hidalgo, J. Bosh, Tetrahedron: Asymmetry 1997, 8, 2237-2240.
21. When more dilute solutions were employed it was necessary to stir the mixture for 6-7 weeks.
22. A. K. Khusid, Zh. Org. Khim. 1987, 23, 126-129.
23. S. Julia, M. Julia, L. Braseur, Bull. Soc. Chim. Fr. 1962, 1634-1638.
24. P. Knochel, P. Y. M. Chang, S. C. Berk, J. Talbert, J. Org. Chem. 1988, 53, 2390-2392.
25. M. Uchida, T. Nishi, K. Nakagana, Eur. Pat. Appl. EP 35,228, 1981. Chem. Abstr. 1982, 96, 6738a.
26. E. Cadis, A. V. Gheorghe, L. Fey, M. Herman, Rev. Chim. 1988, 39, 222-226.
27. N. I. Kapustina, S. S. Spektor, G. Y. Nikishin, Izv. Akad. Nank. Ser. Khim. 1983, 1541-1545.
28. M. T. Reding, S. L. Buchwald, J. Org. Chem. 1998, 63, 6344-6347.
29. M. Schlosser, in Organometallics in Synthesis, J. Wiley, New York, 1994, Chapter 4.
30. C. C. Tseng, S. Terashima, S. I. Yamada, Chem. Pharm. Bull. 1977, 25, 29.
31. M. P. Doyle, A. V. Kalinin, Tetrahedron Lett. 1996, 37, 1371-1374.
32. A. I. Meyers, D. A. Dickman, T. R. Bailey, J. Am. Chem. Soc. 1985, 107, 7974-7978.
33. K. H. Drauz, A. Kleemann, J. Martens, Angew. Chem. Int. Ed. Engl. 1982, 21, 584.
34. S. Arseniyadis, P. Q. Huang, H.-P. Husson, Tetrahedron Lett. 1988, 29, 631.
35. D. W. Armstrong, W. Li, A. M. Stalcup, H. V. Secor, R. R. Izac, J. I. Seeman, Anal. Chim. Acta 1990, 234, 365.
36. C. J. Moody, A. P. Lightfoot, P. T. Gallagher, J. Org. Chem. 1997, 62, 746-748.
37. B. Ringdaht, A. R. Pinder, W. E. Pereira, N. J. Oppenheimer, J. C. Craig, J. Chem. Soc., Perkin Trans. 1 1984, 1-4.
38. M. Mehmandoust, C. Marazano, B. C. Das, J. Chem. Soc., Chem. Commun. 1989, 1185-1187.
39. H. Kunz, W. Pfrengle, Angew. Chem. Int. Ed. Engl. 1989, 28, 1067-1069.