The synthesis of a chiral fluoxetine intermediate by catalytic enantioselective hydrogenation of benzoylacetamide

Tetrahedron Asymmetry

Volumn 9, Issue 10, 1998, Pages 1637-1640

  Huang, Hsiang Ling ^a   Liu, Lee Tai ^a   Chen, Shyh Fong ^a   Ku, Hao ^a  

^a Molecular Biology Division Devmt Center for Biotechnology   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

3 HYDROXY 3 PHENYLPROPANOIC ACID N METHYL AMIDE; 3 OXOPHENYLPROPANOIC ACID N METHYL AMIDE; FLUOXETINE; UNCLASSIFIED DRUG;

ARTICLE; BULIMIA; CATALYST; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; HYDROGENATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0344505762     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00158-X     Document Type: Article

References (17)

1. Shutske, G. M. Exp. Opin. Ther. Patents 1994, 4, 335-341.
2. Molloy, B.; Schmiegel, K. K. US Patent 4314081, 1982.
3. (a) Robertson, D. W.; Jones, N. D.; Swartzendruber, J. K.; Yang, K. S.; Wong, D. T. J. Med. Chem. 1988, 31, 185.
4. (b) Robertson, D. W.; Krushinski, J. H.; Fuller, R. W.; Leander, J. D. J. Med. Chem. 1988, 31, 1412.
5. (a) Sakuraba, S.; Achiwa, K. Chem. Pharm. Bull. 1995, 43, 748-753.
6. (b) Lily Co. Drugs Fut. 1996, 21, 83-85.
7. (a) Srebnik, M.; Ramachandran, P. V.; Brown, H. C. J. Org. Chem. 1988, 53, 2916-2920.
8. (b) Corey, E. J.; Reichard, G. Tetrahedron Lett. 1989, 30, 5207-5210.
9. Devine, P. N.; Heid, R. M.; Tschaen, D. M. Tetrahedron 1997, 53, 6739-6746.
10. (a) Boaz, N. W. J. Org. Chem. 1992, 57, 4289-4292.
11. (b) Raju, S. B.; Chiou, T. W.; Tai, D. F. Tetrahedron: Asymmetry 1995, 6, 1519-1520.
12. (c) Master, H. E.; Newadkar, R. V.; Rane, R. A.; Kumar, A. Tetrahedron Lett. 1996, 37, 9253-9254.
13. (a) Kumar, A.; Ner, D. H.; Dike, S. Tetrahedron Lett. 1991, 32, 1901-1904.
14. (b) Quiros, M.; Rebolledo, F.; Liz, R.; Gotor, V. Tetrahedron: Asymmetry 1997, 8, 3035-3038.
15. Alger, D. J.; Laneman, S. A. Tetrahedron: Asymmetry 1997, 8, 3327-3355.
16. (a) Kitamura, M.; Ohkuma, T.; Inoue, S.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Ohta, T.; Takaya, H.; Noyori, R. J. Am. Chem. Soc. 1988, 110, 629, and references cited therein.
17. (b) Kitamura, M.; Tokunaga, M.; Ohkuma, T.; Noyori, R. Organic Syntheses 1992, 71, 1-13.