Stereoselective synthesis of meso- and cis-2,6-diarylpiperidin-4-ones catalyzed by L-proline

Synthesis

Volumn , Issue 3, 2008, Pages 0479-0484

  Aznar, Fernando ^a   García, Ana Belén ^a   Quiñones, Noelia ^a   Cabal, María Paz ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

2,6 diarylpiperidin 4 ones; Aza Diels Alder; L proline; Nitrogen heterocycles; Organocatalysis

Indexed keywords

DIARYLPIPERIDIN; ORGANOCATALYSIS;

CATALYSIS; NITROGEN COMPOUNDS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

STEREOSELECTIVITY;

1 ALLYL 2 (2 BROMOPHENYL) 6 PHENYLPIPERIDIN 4 ONE; 1 ALLYL 2 (4 CHLOROPHENYL) 6 PHENYLPIPERIDIN 4 ONE; 1 ALLYL 2 (4 FLUOROPHENYL) 6 PHENYLPIPERIDIN 4 ONE; 1 ALLYL 2 (4 METHOXYPHENYL) 6 PHENYLPIPERIDIN 4 ONE; MESO 1 (4 METHOXYPHENYL) 2,6 DIPHENYLPIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 BIS(2 BROMOPHENYL)PIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 BIS(2 IODOPHENYL)PIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 BIS(3,4 DIMETHOXYPHENYL)PIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 BIS(4 CHLOROPHENYL)PIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 BIS(4 FLUOROPHENYL)PIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 BIS(4 METHOXYPHENYL)PIPERIDIN 4 ONE; MESO 1 ALLYL 2,6 DIPHENYLPIPERIDIN 4 ONE; MESO 1 BUT 3 ENYL 2,6 DIPHENYLPIPERIDIN 4 ONE; MESO 1,2,6 TRIPHENYLPIPERIDIN 4 ONE; MESO 2 BUTYL 2,6 DIPHENYLPIPERIDIN 4 ONE; MESO 2,6 BIS(2 IODOPHENYL)PIPERIDIN 4 ONE; MESO 2,6 BIS(4 FLUOROPHENYL)PIPERIDIN 4 ONE; MESO 2,6 BIS(4 METHOXYPHENYL)PIPERIDIN 4 ONE; MESO 2,6 DIPHENYLPIPERIDIN 4 ONE; PIPERIDINE DERIVATIVE; PROLINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; DIASTEREOISOMER; DIELS ALDER REACTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS;

EID: 39349112034     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-990814     Document Type: Article

References (29)

1. (a) Rubiralta, M.; Giralt, E.; Díez, A. Piperidine. Structure, Preparation, Reactivity and Synthetic Applications of Piperidine and its Derivatives; Elsevier: Amsterdam, 1991.
2. (b) Bailey, P. D.; Smith, P. D.; Morgan, K. M.; Rosair, G. M. Tetrahedron Lett. 2002, 43, 1071.
3. (c) Amat, M.; Llor, N.; Hidalgo, J.; Escolano, C.; Bosch, J. J. Org. Chem. 2003, 68, 1919.
4. (a) Tortolani, D. R.; Poss, M. A. Org. Lett. 1999, 1, 1261.
5. (b) Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953.
6. (c) Jagt, R. B. C.; Vries, J. G.; Feringa, B. L.; Minnaard, A. J. Org. Lett. 2005, 7, 2433.
7. (a) Ganellin, C. R.; Spickett, R. G. J. Med. Chem. 1965, 8, 619.
8. (b) Ishimaru, K.; Kojima, T. J. Chem. Soc., Perkin Trans. 1 2000, 2105.
9. (c) Rameshkumar, N.; Veena, A.; Ilavarasan, R.; Adiraj, M.; Shanmugapandiyan, P.; Sridhar, S. K. Biol. Pharm. Bull. 2003, 26, 188.
10. (d) Ramalingan, C.; Balasubramanian, S.; Kabilan, S.; Vasudevan, M. Eur. J. Med. Chem. 2004, 34, 527.
11. (a) Baliah, V.; Jeyaraman, R.; Chandrasekaran, L. Chem. Rev. 1983, 83, 379.
12. (b) Vijayabaskar, V.; Perumal, S.; Devanathan, V. C. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1995, 34, 649.
13. (c) Ciblat, S.; Besse, P.; Canet, J. L.; Troin, Y.; Veschambre, H.; Gelas, J. Tetrahedron: Asymmetry 1999, 10, 2225.
14. (d) Ma, D.; Sun, H. Org. Lett. 2000, 2, 2503.
15. (e) Davis, F. A.; Chao, B.; Rao, A. Org. Lett. 2001, 3, 3169.
16. (f) Ma, D.; Ma, N. Tetrahedron Lett. 2003, 44, 3963.
17. (g) Davis, F. A.; Rao, A.; Carroll, P. J. Org. Lett. 2003, 5, 3855.
18. (a) List, B. Synlett 2001, 1675.
19. (b) List, B. Tetrahedron 2002, 58, 5573.
20. (c) Notz, W.; Tanaka, F.; Barbas, C. F. III Acc. Chem. Res. 2004, 37, 580.
21. (d) Sundén, H.; Ibrahem, I.; Eriksson, L.; Córdova, A. Angew. Chem. Int. Ed. 2005, 44, 4877.
22. (a) Barluenga, J.; Aznar, F.; Cabal, M.-P.; Valdés, C. J. Org. Chem. 1993, 58, 3391.
23. (b) Barluenga, J.; Aznar, F.; Ribas, C.; Valdés, C.; Fernández, M.; Cabal, M.-P.; Trujillo, J. Chem. Eur. J. 1996, 2, 805.
24. (c) García, A.-B.; Valdés, C.; Cabal, M.-P. Tetrahedron Lett. 2004, 45, 4357.
25. Aznar, F.; García, A.-B.; Cabal, M.-P. Adv. Synth. Catal. 2006, 348, 2443.
26. Alcaide, B.; Almendros, P.; Alonso, J. M.; Aly, M. F. Org. Lett. 2001, 3, 3781.
27. Drake, N. L.; Allen, P. Org. Synth. Coll. Vol. I; John Wiley & Sons: London, 1932, 77.
28. (a) For the preparation of N-alkylimines, see: Look, G. C.; Murphy, M. M.; Campbell, D. A.; Gallop, M. A. Tetrahedron Lett. 1995, 36, 2937.
29. (b) For the preparation of N-arylimines, see: Bigelow, L. A.; Eatough, H. Org. Synth. Coll. Vol. I; John Wiley & Sons: London, 1932, 80.