A concise procedure for the preparation of enantiopure 3-alkylpiperidines

Tetrahedron Asymmetry

Volumn 8, Issue 13, 1997, Pages 2237-2240

  Amat, Mercedes ^a   Llor, Núria ^a   Hidalgo, José ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

PIPERIDINE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030801479     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00204-8     Document Type: Article

References (21)

1. (a) Schneider, M. J. In Alkaloids, Chemical and Biological Perspectives, Pelletier, S. W., Ed.; Pergamon, 1996; Vol. 10, Chapter 2;
2. (b) Andersen, R. J.; Van Soest, R. W. M.; Kong, F. Ibid, Chapter 3.
3. Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4.
4. Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4.
5. (a) Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223.
6. (b) Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977.
7. (c) Amat, M.; Hidalgo, J.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 1845.
8. (d) Amat, M.; Pshenichnyi, G.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 3091.
9. For other reports on the preparation of 1, see: (a) Royer, J.; Husson, H.-P.; Heterocycles 1993, 36, 1493;
10. (b) Micouin, L.; Quirion, J.-C.; Husson, H.-P. Synth. Commun. 1996, 26, 1605.
11. For other recent reports on the preparation of enantiopure 3-alkylpiperidines, see: (a) Micouin, L.; Varea, T.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2529;
12. (b) Palmisano, G.; Santagostino, M.; Riva, S.; Sisti, M. Tetrahedron: Asymmetry 1995, 6, 1229;
13. (c) Sakagami, H.; Samizu, K.; Kamikubo, T.; Ogasawara, K. Synlett 1996, 163;
14. (d) Wong, Y.-S.; Marazano, C.; Gnecco, D.; Génisson, Y.; Chiaroni, A.; Das, B. C. J. Org. Chem. 1997, 62, 729.
15. This ester was prepared by reaction of the piperidine enamine of butanal with methyl acrylate: Norman, M. H.; Heathcock, C.H. J. Org. Chem. 1988, 53, 3370.
16. As could be expected, when the reaction was performed with racemic phenylglycinol, a 9:1 mixture of racemic oxazolopiperidones 4a and 4b was obtained.
17. For related 'deracemizations', see: (a) Ragan, J. A.; Claffey, M. C. Heterocycles 1995, 41, 57.
18. (b) Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Old, D. W.; Mooney, P. A. J. Org. Chem. 1996, 61, 5813.
19. 1H-NMR after the initial reaction at 0°C.
20. (a) For the equilibration of (R)-phenylglycinol-derived 2,4-disubstituted oxazolidines to the cis-isomer, see: Arséniyadis, S.; Huang, P. Q.; Morellet, N.; Beloeil, J.-C.; Husson, H.-P. Heterocycles 1990, 31, 1789.
21. (b) For a related equilibration, see: Takahashi, H.; Tsubuki, T.; Higashiyama, K. Heterocycles 1992, 33, 281.