An unexpected oxidation in the generation of cyclopenta[c]piperidines by ring-closing metathesis

Organic Letters

Volumn 11, Issue 19, 2009, Pages 4370-4373

  Amat, Mercedes ^a   Brunaccini, Elisa ^a   Checa, Begoña ^a   Pérez, Maria ^a   Llor, Núria ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CONFORMATION; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; MOLECULAR CONFORMATION; OXIDATION-REDUCTION; PIPERIDINES; STEREOISOMERISM;

EID: 70350173755     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol901704f     Document Type: Article

References (29)

1. For reviews, see: (a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503-9569.
2. (b) Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1-8.
3. (c) Groaning, M. D.; Meyers, A. I. Tetrahedron 2000, 56, 9843-9873.
4. (d) Escolano, C.; Amat, M.; Bosch, J. Chem. - Eur. J. 2006, 12, 8198-8207. For more recent work, see:
5. (e) Amat, M.; Pérez, M.; Minaglia, A. T.; Peretto, B.; Bosch, J. Tetrahedron 2007, 63, 5839-5848.
6. (f) Amat, M.; Lozano, O.; Escolano, C.; Molins, E.; Bosch, J. J. Org. Chem. 2007, 72, 4431-4439.
7. (g) Amat, M.; Santos, M. M. M.; Bassas, O.; Llor, N.; Escolano, C.; Gómez-Esqué, A.; Molins, E.; Allin, S. M.; McKee, V.; Bosch, J. J. Org. Chem. 2007, 72, 5193-5201.
8. (h) Amat, M.; Pérez, M.; Minaglia, A. T.; Bosch, J. J. Org. Chem. 2008, 73, 6920-6923.
9. (i) Amat, M.; Griera, R.; Fabregat, R.; Molins, E.; Bosch, J. Angew. Chem., Int. Ed. 2008, 47, 3348-3351.
10. (j) Amat, M.; Fabregat, R.; Griera, R.; Bosch, J. J. Org. Chem. 2009, 74, 1794-1797.
11. (k) Amat, M.; Gómez-Esqué, A.; Escolano, C.; Santos, M, M. M.; Molins, E.; Bosch, J. J. Org. Chem. 2009, 74, 1205-1211.
12. Amat, M.; Checa, B.; Llor, N.; Molins, E.; Bosch, J. Chem. Commun, 2009, 2935-2937.
13. Coombs, T. C.; Lee, M. D.; Wong, H.; Armstrong, M.; Cheng, B.; Chen, W.; Moretto, A. F.; Liebeskind, L. S. J. Org. Chem. 2008, 73, 882-888.
14. Amat, M.; Pérez, M.; Llor, N.; Bosch, J.; Lago, E.; Molins, E. Org. Lett. 2001, 3, 611-614.
15. (a) Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, 1983; p 221.
16. (b) Perlmutter, P. Conjugate Addition Reactions in Organic Synthesis; Pergamon Press: Oxford, 1992; p 25.
17. (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim. 2003; volumesl-3.
18. (b) Felpin, F.-X.; Lebreton, J. Eur. J. Org. Chem. 2003, 3693-3712.
19. (c) Deiters, A.; Martin, S.F. Chem. Rev. 2004, 104, 2199-2238.
20. The residual oxygen in the solvent and/or the manipulation during workup and column chromatography purification could account for the observed oxidation .
21. For a study of the effect of strain in the spontaneous oxygenation of cyclic olefins, see: Bartlett, P. D.; Banavali, R. J. Org. Chem. 1991, 56, 6043-6050.
22. A double-bond isomerization was observed in. the cyclohepta series to give mixtures of c and c′ isomers. For related isomerizations in RCM. reactions, see: (a) Schmidt, B. J. Org. Chem. 2004, 69, 7672-7687.
23. (b) Hong, S. H.; Sanders, D. P.; Lee, C. W.; Grubbs, R. H. J. Am. Chem. Soc. 2005, 127, 17160-17161.
24. (c) Fustero, S.; Sánchez-Roselló, M.; Jiménez, D.; Sanz-Cervera, J. F.; del Pozo, C.; Aceña, J. L. J. Org. Chem. 2006, 71, 2706-2714.
25. (a) Dickinson, E. M.; Jones, G. Tetrahedron 1969, 25, 1523-1529.
26. (b) Harris, G. H.; Fixman, E. C.; Stermitz, R R.; Castedo, L. J. Nat. Prod. 1988, 51, 543-548.
27. (c) Lins, A. P.; Felicio, J. D. Phytochemistry 1993, 34, 876-878.
28. (d) Kam, T.-S.; Yoganathan, K.; Wei, C. J. Nat. Prod. 1997, 60, 673-676.
29. Only one enantioselective synthesis of (+)-tecomanine has been reported: Kametani, T.; Suzuki, Y.; Ban, C.; Honda, T. Heterocvcles 1987, 26, 1491-1493.