Design of resolving reagents: p-substituted mandelic acids as resolving reagents for 1-arylalkylamines

Tetrahedron Asymmetry

Volumn 7, Issue 6, 1996, Pages 1539-1542

  Kinbara, Kazushi ^a   Sakai, Kenichi ^b   Hashimoto, Yukihiko ^a   Nohira, Hiroyuki ^b   Saigo, Kazuhiko ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b SAITAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

4 METHOXYMANDELIC ACID; 4 METHYLMANDELIC ACID; ARALKYLAMINE; MANDELIC ACID DERIVATIVE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL;

EID: 0029950959     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00175-9     Document Type: Article

References (12)

1. Jacques, J.; Collet, A.; Wilen, S. H. Enantiomers, Racemates, and Resolutions; Krieger Publishing Company: Malabar, Florida 1994.
2. ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508. Gharpure, M. M.; Rao, A. S. Synthesis 1988, 410. van der Haest, A. D.; Wynberg, H.; Leusen, F. J. J.; Bruggink, A. Recl. Trav. Chim. Pays-Bas 1993, 112, 230. Kozma, D.; Acs, M.; Fogassy, E. Tetrahedron 1994, 50, 6907.
3. ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508. Gharpure, M. M.; Rao, A. S. Synthesis 1988, 410. van der Haest, A. D.; Wynberg, H.; Leusen, F. J. J.; Bruggink, A. Recl. Trav. Chim. Pays-Bas 1993, 112, 230. Kozma, D.; Acs, M.; Fogassy, E. Tetrahedron 1994, 50, 6907.
4. ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508. Gharpure, M. M.; Rao, A. S. Synthesis 1988, 410. van der Haest, A. D.; Wynberg, H.; Leusen, F. J. J.; Bruggink, A. Recl. Trav. Chim. Pays-Bas 1993, 112, 230. Kozma, D.; Acs, M.; Fogassy, E. Tetrahedron 1994, 50, 6907.
5. ten Hoeve, W.; Wynberg, H. J. Org. Chem. 1985, 50, 4508. Gharpure, M. M.; Rao, A. S. Synthesis 1988, 410. van der Haest, A. D.; Wynberg, H.; Leusen, F. J. J.; Bruggink, A. Recl. Trav. Chim. Pays-Bas 1993, 112, 230. Kozma, D.; Acs, M.; Fogassy, E. Tetrahedron 1994, 50, 6907.
6. Newman, P. Optical Resolution Procedures for Chemical Compounds; Optical Resolution Information Center: New York 1981; Vol. 1.
7. Saigo, K.; Ogawa, S.; Kikuchi, S.; Kasahara, A.; Nohira, H. Bull. Chem. Soc. Jpn. 1982, 55, 1568. Sudo, A.; Hashimoto, Y.; Kimoto, H.; Hayashi, K.; Saigo, K. Tetrahedron Asym. 1994, 5, 1333.
8. Saigo, K.; Ogawa, S.; Kikuchi, S.; Kasahara, A.; Nohira, H. Bull. Chem. Soc. Jpn. 1982, 55, 1568. Sudo, A.; Hashimoto, Y.; Kimoto, H.; Hayashi, K.; Saigo, K. Tetrahedron Asym. 1994, 5, 1333.
9. Sakai, K.; Hashimoto, Y.; Kinbara, K.; Saigo, K.; Murakami, H.; Nohira, H. Bull. Chem. Soc. Jpn. 1993, 66, 3414.
10. Since there is a possibility that the resolution efficiency depends on the solvent to some extent, we restricted the solvent to protic one, such as water, methanol, or their mixture, which would play a similar role to each other in solvation etc. and control the solubility of the diastereomeric salts.
11. Hoover, J. R. E.; Dunn, G. L.; Jakas, D. R.; Lam, L. L.; Taggart, J. J.; Guarini J. R.; Phillips, L. J. Med. Chem. 1974, 17, 34.
12. 7 (S)-11 (95% e.e.) and (R)-12 (95% e.e.) were obtained and used for the resolutions in the present study.