Efficient enantiomeric resolution via introduction of a fluorous tag as a resolving reagent with β-cyclodextrin columns: Model study on fluorinated O-acetylmandelate and ibuprofen amide

Tetrahedron Letters

Volumn 44, Issue 33, 2003, Pages 6227-6230

  Matsuzawa, Hiroshi ^a   Mikami, Koichi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Fluorine chemistry; Liquid chromatography; Optical resolution; cyclodextrin

Indexed keywords

AMIDE; BETA CYCLODEXTRIN; IBUPROFEN; IBUPROFEN AMIDE; MANDELIC ACID DERIVATIVE; O ACETYLMANDELATE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; FLUORINATION; OPTICAL RESOLUTION; RACEMIC MIXTURE;

EID: 0041346154     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01538-7     Document Type: Article

References (16)

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6. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
7. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
8. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
9. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
10. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
11. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
12. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
13. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
14. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
15. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.
16. Review: (a) Yoshida, J.; Itami, K. Chem. Rev. 2002, 102, 3693; (b) Gradysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823; (c) Dobbs, A. P. M.; Kimberley, R. J. Fluorine Chem. 2002, 118, 3; (d) Curran, D. P.; Lee, Z. Green Chem. 2001, G3; (e) Curran, D. P. Synlett 2001, 1488; (f) Kitazume, T. J. Flurorine Chem. 2000, 105, 265; (g) Fish, R. H. Chem. Eur. J. 1999, 5, 1677; (h) Cavazzini, M.; Montanari, F.; Pozzi, G.; Quici, S. J. Fluorine Chem. 1999, 94, 183; (i) de Wolf, E.; van Koten, G.; Deelman, B.-J. Chem. Soc. Rev. 1999, 28, 37; (j) Curran, D. P. Angew. Chem. Int. Ed. Engl, 1998, 37, 1174; (k) Horváth, I. T. Acc. Chem. Res. 1998, 31, 641.