Enzymatic resolution of substituted mandelic acids

Tetrahedron Letters

Volumn 44, Issue 29, 2003, Pages 5477-5481

  Campbell, Robert F ^a   Fitzpatrick, Kevin ^a   Inghardt, Tord ^b   Karlsson, Olle ^b   Nilsson, Kristina ^b   Reilly, John E ^a   Yet, Larry ^a  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

^b ASTRAZENECA R AND D   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

3 (METHYLTHIO)MANDELIC ACID; 3 CHLORO 5 (PYRROL 1 YL)MANDELIC ACID; 3 CHLORO 5 DIMETHYLAMINOMANDELIC ACID; 3 CHLORO 5 NITROMANDELIC ACID; 3 DIMETHYLAMINO 5 (TRIFLUOROMETHYL)MANDELIC ACID; 3 NITROMANDELIC ACID; ENZYME; MANDELIC ACID DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ARTICLE; ENZYME MECHANISM; SYNTHESIS;

EID: 0037525438     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01270-X     Document Type: Article

References (18)

1. For reviews on the use of lipases in organic synthesis, see: (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63; (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695; (c) Boland, W.; Frössl, C.; Lorentz, M. Synthesis 1991, 1049; (d) Faber, K.; Riva, S. Synthesis 1992, 895; (e) Theil, F. Chem. Rev. 1995, 95, 2203; (f) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
2. For reviews on the use of lipases in organic synthesis, see: (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63; (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695; (c) Boland, W.; Frössl, C.; Lorentz, M. Synthesis 1991, 1049; (d) Faber, K.; Riva, S. Synthesis 1992, 895; (e) Theil, F. Chem. Rev. 1995, 95, 2203; (f) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
3. For reviews on the use of lipases in organic synthesis, see: (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63; (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695; (c) Boland, W.; Frössl, C.; Lorentz, M. Synthesis 1991, 1049; (d) Faber, K.; Riva, S. Synthesis 1992, 895; (e) Theil, F. Chem. Rev. 1995, 95, 2203; (f) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
4. For reviews on the use of lipases in organic synthesis, see: (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63; (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695; (c) Boland, W.; Frössl, C.; Lorentz, M. Synthesis 1991, 1049; (d) Faber, K.; Riva, S. Synthesis 1992, 895; (e) Theil, F. Chem. Rev. 1995, 95, 2203; (f) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
5. For reviews on the use of lipases in organic synthesis, see: (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63; (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695; (c) Boland, W.; Frössl, C.; Lorentz, M. Synthesis 1991, 1049; (d) Faber, K.; Riva, S. Synthesis 1992, 895; (e) Theil, F. Chem. Rev. 1995, 95, 2203; (f) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
6. For reviews on the use of lipases in organic synthesis, see: (a) Sih, C. J.; Wu, S. H. Topics Stereochem. 1989, 19, 63; (b) Chen, C.-S.; Sih, C. J. Angew. Chem., Int. Ed. Engl. 1989, 28, 695; (c) Boland, W.; Frössl, C.; Lorentz, M. Synthesis 1991, 1049; (d) Faber, K.; Riva, S. Synthesis 1992, 895; (e) Theil, F. Chem. Rev. 1995, 95, 2203; (f) Schmid, R. D.; Verger, R. Angew. Chem., Int. Ed. Engl. 1998, 37, 1608.
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10. For an example of the enzymatic resolution of an α-hydroxy carboxylic acid using Lipase PS 'Amano', see: Chadha A., Manohar M. Tetrahedron: Asymmetry. 6:1995;651.
11. Lipase PS 'Amano' (Pseudomonas cepacia; Lot No. LPSAW09505) was purchased from Amano Pharmaceutical Co., Ltd, Nagoya, Japan.
12. For examples of the use of enzymes in the resolution of mandelic acid and mandelate esters, see: (a) Strauss, U. T.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 4079; (b) Zhang, W.; Wang, P. G. J. Org. Chem. 2000, 65, 4732; (c) Queiroz, N.; da Graça Nascimento, M. Tetrahedron Lett. 2002, 43, 5225.
13. For examples of the use of enzymes in the resolution of mandelic acid and mandelate esters, see: (a) Strauss, U. T.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 4079; (b) Zhang, W.; Wang, P. G. J. Org. Chem. 2000, 65, 4732; (c) Queiroz, N.; da Graça Nascimento, M. Tetrahedron Lett. 2002, 43, 5225.
14. For examples of the use of enzymes in the resolution of mandelic acid and mandelate esters, see: (a) Strauss, U. T.; Faber, K. Tetrahedron: Asymmetry 1999, 10, 4079; (b) Zhang, W.; Wang, P. G. J. Org. Chem. 2000, 65, 4732; (c) Queiroz, N.; da Graça Nascimento, M. Tetrahedron Lett. 2002, 43, 5225.
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17. For additional experimental details, including spectroscopic data, and additional examples, see: Inghardt, T.; Nyström, J.-E. World Patent WO 0042059, 2000.
18. Depending on the chromatography eluents used and the drying time, products may have been isolated as their ammonium salts. When necessary, salts were neutralized in a separatory funnel with aqueous acid or by passing through a weakly acidic ion exchange resin.