Synthesis of α-phenyl-1-(R)-(-)-piperidineacetic esters

Tetrahedron Asymmetry

Volumn 8, Issue 2, 1997, Pages 203-206

  Juárez, Jorge ^a   Gnecco, Dino ^a   Galindo, Alberto ^a   Enríquez, Raúl G ^b   Marazano, Christian ^c   Reynolds, William F ^d  

^a BENEMÉRITA UNIVERSIDAD AUTÓNOMA DE PUEBLA   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^c CNRS   (France)

^d UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

PHENYLACETIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031019992     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00474-0     Document Type: Article

References (13)

1. Blicke, F. F.; Faust, J. A.; Raffelson, H. J. Am. Chem. Soc. 1954, 76, 3156; ibid. 1954, 76, 3161.
2. Blicke, F. F.; Faust, J. A.; Raffelson, H. J. Am. Chem. Soc. 1954, 76, 3156; ibid. 1954, 76, 3161.
3. Kevin, K.; Robert, N. B.; Durst, T. Tetrahedron Lett. 1994, 35, 3, 375, and references therein; Chabrier, P.; Najer, H.; Giudicelli, R.; Joannic, M. Bull. Soc. Chim. France 1957, 1365; Najer, H.; Chabrier, P.; Giudicelli, R. Bull. Soc. Chim. France 1958, 355.
4. Kevin, K.; Robert, N. B.; Durst, T. Tetrahedron Lett. 1994, 35, 3, 375, and references therein; Chabrier, P.; Najer, H.; Giudicelli, R.; Joannic, M. Bull. Soc. Chim. France 1957, 1365; Najer, H.; Chabrier, P.; Giudicelli, R. Bull. Soc. Chim. France 1958, 355.
5. Kevin, K.; Robert, N. B.; Durst, T. Tetrahedron Lett. 1994, 35, 3, 375, and references therein; Chabrier, P.; Najer, H.; Giudicelli, R.; Joannic, M. Bull. Soc. Chim. France 1957, 1365; Najer, H.; Chabrier, P.; Giudicelli, R. Bull. Soc. Chim. France 1958, 355.
6. Sommer, H. Z.; Jackson, I. L. J. Org. Chem. 1970, 35, 1558 and references therein.
7. Juaristi, E.; Madrigal, D. Tetrahedron 1989, 45, 629.
8. Grant, G. S.; Thipamon, S. J. Org. Chem. 1983, 48, 627; Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853 and references therein.
9. Grant, G. S.; Thipamon, S. J. Org. Chem. 1983, 48, 627; Nagai, Y.; Kusumi, T. Tetrahedron Lett. 1995, 36, 1853 and references therein.
10. The reaction was always carried out in tert-butanol because other alcohols induce up to ca. 50% trans-esterification.
11. The use of triethylamine at a maximum temperature of 45°C was found suitable for avoiding racemization of the aminoacid ester.
12. Jens, A.; Peter, S. Tetrahedron 1995, 51, 9747.
13. 3): 10.7 (br, 1H), 7.44 (s, 5H), 5.26 (br, 1H), 4.46 (m, 2H), 4.10 (d, 1H), 3.73 (d, 1H), 3.59 (d, br, 1H), 2.69 (t, br, 1H), 2.45 (m, 2H), 2.29 (dt, 1H), 1.84 (m, br, 3H), 1.28 (m, 1H).