Synthesis of Enantiopure trans-3,4-Disubstituted Piperidines. An Enantiodivergent Synthesis of (+)- And (-)-Paroxetine

Journal of Organic Chemistry

Volumn 65, Issue 10, 2000, Pages 3074-3084

  Amat, Mercedes ^a   Bosch, Joan ^a   Hidalgo, José ^a   Cantó, Margalida ^a   Pérez, Maria ^a   Llor, Núria ^a   Molins, Elies ^b   Miravitlles, Carles ^b   Orozco, Modesto ^a   Luque, Javier ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FEMOXETINE; LACTAM DERIVATIVE; PAROXETINE; PIPERIDINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CONJUGATION; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; STEREOCHEMISTRY;

ANTIDEPRESSIVE AGENTS, SECOND-GENERATION; INDICATORS AND REAGENTS; PAROXETINE; PIPERIDINES; STEREOISOMERISM;

EID: 0034685859     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991816p     Document Type: Article

References (14)

1. (a) Jones, T. H.; Blum, M. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1983; Vol. 1, Chapter 2, pp 33-84.
2. (b) Fodor, G. B.; Colasanti, B. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1985; Vol. 3, Chapter 1, pp 1-90.
3. (c) Strunz, G. M.; Findlay, J. A. In The Alkaloids; Brossi, A., Ed.; Academic Press: London, 1985; Vol. 26, Chapter 3, pp 89-183.
4. (d) Angle, R. S.; Breitenbucher, J. G. In Studies in Natural Products Chemistry. Stereoselective Synthesis (Part J); Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1995; Vol. 16, pp 453-502.
5. (e) Schneider, M. J. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Wiley: New York, 1996; Vol. 10, Chapter 3, pp 155-355.
6. Amat, M.; Llor, N.; Bosch, J. Tetrahedron Lett. 1994, 35, 2223.
7. Amat, M.; Llor, N.; Hidalgo, J.; Hernández, A.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 977.
8. Amat, M.; Hidalgo, J.; Llor, N.; Bosch, J. Tetrahedron: Asymmetry 1998, 9, 2419.
9. Amat, M.; Pshenichnyi, G.; Bosch, J.; Molins, E.; Miravitlles, C. Tetrahedron: Asymmetry 1996, 7, 3091.
10. For a preliminary account of a part of this work, see: Amat, M.; Hidalgo, J.; Bosch, J. Tetrahedron: Asymmetry 1996, 7, 1845.
11. For reviews, see: a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Meyers, A. I. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell Scientific Publications: Oxford, 1994; pp 145- 161.
12. For reviews, see: a) Romo, D.; Meyers, A. I. Tetrahedron 1991, 47, 9503. (b) Meyers, A. I. In Stereocontrolled Organic Synthesis; Trost, B. M., Ed.; Blackwell Scientific Publications: Oxford, 1994; pp 145-161.
13. For a review, see: Meyers, A. I.; Brengel, G. P. Chem. Commun. 1997, 1.
14. Meyers, A. I.; Lefker, B. A.; Sowin, T. J.; Westrum, L. J. J. Org. Chem. 1989, 54, 4243.