A novel chiral base mediated glutarimide desymmetrisation: Application to the asymmetric synthesis of (-)-paroxetine

Synlett

Volumn , Issue 12, 2002, Pages 2074-2076

  Greenhalgh, Daniel A ^a   Simpkins, Nigel S ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Asymmetric synthesis; Chiral lithium amide; Glutarimide; Kinetic resolution; Paroxetine

Indexed keywords

AMIDE; GLUTARIMIDE; LITHIUM; PAROXETINE; SEROTONIN UPTAKE INHIBITOR;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0036458253     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-35588     Document Type: Article

References (16)

1. (a) Adams, D. J.; Simpkins, N. S.; Smith, T. J. N. Chem. Commun. 1998, 1605.
2. (b) For our full report of this work, see: Adams, D. J.; Blake, A. J.; Cooke, P. A.; Gill, C. D.; Simpkins, N. S. Tetrahedron 2002, 58, 4603; this issue of the journal is dedicated entirely to chiral base chemistry and is an excellent source of leading references in the area.
3. For recent asymmetric syntheses of paroxetine, see: (a) de Gonzalo, G.; Brieva, R.; Sanchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947. (b) Cossy, J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 7805. (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. (d) Liu, L. T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L. W.; Wen, Y.-S. Tetrahedron: Asymmetry 2001, 12, 419. (e) Amat, M.; Bosch, J.; Hidalgo, J.; Canto, M.; Perez, M.; Llor, N.; Molins, E.; Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
4. For recent asymmetric syntheses of paroxetine, see: (a) de Gonzalo, G.; Brieva, R.; Sanchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947. (b) Cossy, J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 7805. (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. (d) Liu, L. T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L. W.; Wen, Y.-S. Tetrahedron: Asymmetry 2001, 12, 419. (e) Amat, M.; Bosch, J.; Hidalgo, J.; Canto, M.; Perez, M.; Llor, N.; Molins, E.; Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
5. For recent asymmetric syntheses of paroxetine, see: (a) de Gonzalo, G.; Brieva, R.; Sanchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947. (b) Cossy, J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 7805. (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. (d) Liu, L. T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L. W.; Wen, Y.-S. Tetrahedron: Asymmetry 2001, 12, 419. (e) Amat, M.; Bosch, J.; Hidalgo, J.; Canto, M.; Perez, M.; Llor, N.; Molins, E.; Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
6. For recent asymmetric syntheses of paroxetine, see: (a) de Gonzalo, G.; Brieva, R.; Sanchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947. (b) Cossy, J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 7805. (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. (d) Liu, L. T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L. W.; Wen, Y.-S. Tetrahedron: Asymmetry 2001, 12, 419. (e) Amat, M.; Bosch, J.; Hidalgo, J.; Canto, M.; Perez, M.; Llor, N.; Molins, E.; Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
7. For recent asymmetric syntheses of paroxetine, see: (a) de Gonzalo, G.; Brieva, R.; Sanchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947. (b) Cossy, J.; Mirguet, O.; Gomez Pardo, D.; Desmurs, J.-R. Tetrahedron Lett. 2001, 42, 7805. (c) Johnson, T. A.; Curtis, M. D.; Beak, P. J. Am. Chem. Soc. 2001, 123, 1004. (d) Liu, L. T.; Hong, P.-C.; Huang, H.-L.; Chen, S.-F.; Wang, C.-L. W.; Wen, Y.-S. Tetrahedron: Asymmetry 2001, 12, 419. (e) Amat, M.; Bosch, J.; Hidalgo, J.; Canto, M.; Perez, M.; Llor, N.; Molins, E.; Miravitlles, C.; Orozco, M.; Luque, J. J. Org. Chem. 2000, 65, 3074.
8. (a) Rama Rao, R.; Singh, A. K.; Varaprasad, C. V. N. S. Tetrahedron Lett. 1991, 32, 4393.
9. (b) Goehring, R. R.; Greenwood, T. D.; Nwokogu, G. C.; Pisipati, J. S.; Rogers, T. G.; Wolfe, J. F. J. Med. Chem. 1990, 33, 926.
10. Bambridge, K.; Begley, M. J.; Simpkins, N. S. Tetrahedron Lett. 1994, 35, 3391.
11. 4F requires 355.1220. The enantiomeric excess was determined by HPLC analysis using a Chiralcel OD column with 3% EtOH in hexane as eluant, at a flow rate of 0.8 mL/min, using UV detection at 215 nm. Retention times were 75.8 min(minor) and 88.5 min(major).
12. The use of bis-lithiated base 8 may seem to invite the formation of unwanted products 7 but we achieved much poorer yields of desired compounds 5 by using the base in mono-lithiated form.
13. Kamikawa, T.; Hayashi, T. Tetrahedron 1999, 55, 3455.
14. Gotov, B.; Schmalz, H.-G. Org. Lett. 2001, 3, 1753.
15. 2 and references therein.
16. 2e