The Stereochemistry of the Addition of Chlorotitanium Enolates of N-Acyl Oxazolidin-2-ones to 5- and 6- Membered N-Acyliminium Ions

Journal of the Brazilian Chemical Society

Volumn 12, Issue 5, 2001, Pages 634-651

  Pilli, Ronaldo A ^a   Böckelmann, Maria Alice ^a   Alves, Conceição De Fatima ^a  

^a UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

2 substituted pyrrolidines and piperidines; Cyclic N acyliminium ions; Oxazolidin 2 ones; Titanium (IV) enolates

Indexed keywords

EID: 0347032812     PISSN: 01035053     EISSN: None     Source Type: Journal    
DOI: 10.1590/S0103-50532001000500007     Document Type: Article

References (42)

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27. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
28. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
29. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
30. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
31. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
32. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
33. For racemic syntheses of metilphenidate see, inter alia: a) Dias, L. C., Fernandes, A. M. A. P., Synth. Commun. 2000, 30, 1311 : For asymmetric syntheses, see: b) Prashad, M.; Har, D.; Ropic, O.; Blacklock, T. J.; Giannousis, P. Tetrahedron: Asymmetry 1998, 9, 2133; c) Faulconbridge, S.; Zavareh, H.; Evans, G.; Langston, M. PCT Int. Appl. Chem. Abstr. 1998, 129, 67705; d) Langston, M.; Zavareh, H. PCT Int. Appl. Chem. Abstr. 1997, 127, 205477; c) Zavareh, H. PCT Int. Appl. Chem. Abtr. 1997, 127, 278144; f) Thai, D. L.; Sapko, M. T.; Reiter, C. T.; Bierer, D. E.; Perel, J. M. J.Med. Chem. 1998, 41, 591; g) Prashad, M.; Kim, H.; Lu, Y.; Har, D.; Repic, O.; Blacklock, T. J.; Giannousis, P. J. Org. Chem. 1999, 64, 1750; h) Davies, H. M. L.; Hansen, T.; Hopper, D. W.; Panaro, S. A. J. Am. Chem. Soc. 1999, 121, 6509; i) Axten, J. M.; Ivy, R.; Krim. L.; Winkler, J. D. J. Am. Chem. Soc. 1999, 121, 6511.
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