The synthesis of (R)- and (S)-α-trifluoromethyl-α-hydroxycarboxylic acids via enzymatic resolutions

Tetrahedron Asymmetry

Volumn 10, Issue 4, 1999, Pages 679-687

  Konigsberger, Kurt ^a   Prasad, Kapa ^a   Repič, Oljan ^a  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; ENZYME; NITRILE; TRIACYLGLYCEROL LIPASE;

ARTICLE; ENANTIOMER; ENZYME CHEMISTRY; HYDROLYSIS; METHODOLOGY; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033605026     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(99)00017-8     Document Type: Article

References (15)

1. For leading references see: Johnson, C. R. Acc. Chem. Res. 1998, 31, 333.
2. McCoy, M. Chem. Eng. News 1998, 76(25), 13.
3. Darrell, R. A.; Smith, F.; Stacey, M.; Tatlow, J. C. J. Chem. Soc. 1951, 2329.
4. Ohnmacht, C.-J.; Russell, K.; Empfield, J. R.; Frank, C. A.; Gibson, K. H. et al. J. Med. Chem. 1996, 39, 4592.
5. (a) Brieden, W.; Naughton, A.; Robins, K.; Shaw, N.; Tinschert, A.; Zimmermann, T. DE 197 35 802 A1, January 15, 1998. Hydrolysis of rac-2b with esterase from Candida lipolytica afforded (R)-1a (71% e.e.) and the unreacted (S)-2b (97% e.e., 59% yield, with respect to half of the starting amount), (b) Crosby, J.; Holt, R. A.; Pittam, J. D. WO 97/38124, October 16, 1997. The authors describe kinetic resolution of rac-2 (R=Me, Et, Bu, R′=Me) with a series of hydrolases with low selectivities, obtaining (R)-acid and (S)-ester in every case. Hydrolysis of rac-4b with PPL (80 wt %, 3 days) gave (S)-4b (19%, e.e. >95%).
6. Resolutions of α,α-disubstituted α-hydroxycarboxylic acid esters have been performed successfully with a series of enzymes: (a) Moorlag, H.; Kellogg, R. M.; Kloosterman, M.; Kaptein, B.; Kamphuis, J.; Shoemaker, H. E. J. Org. Chem. 1990, 55, 5878. (b) Feichter, C.; Faber, K.; Griengl, H. J. Chem. Soc., Perkin Trans. 1 1991, 653. (c) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525. (d) Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643. (f) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365. (g) Pottie, M.; Van der Eycken, J.; Vanewalle, M.; Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319.
7. Resolutions of α,α-disubstituted α-hydroxycarboxylic acid esters have been performed successfully with a series of enzymes: (a) Moorlag, H.; Kellogg, R. M.; Kloosterman, M.; Kaptein, B.; Kamphuis, J.; Shoemaker, H. E. J. Org. Chem. 1990, 55, 5878. (b) Feichter, C.; Faber, K.; Griengl, H. J. Chem. Soc., Perkin Trans. 1 1991, 653. (c) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525. (d) Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643. (f) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365. (g) Pottie, M.; Van der Eycken, J.; Vanewalle, M.; Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319.
8. Resolutions of α,α-disubstituted α-hydroxycarboxylic acid esters have been performed successfully with a series of enzymes: (a) Moorlag, H.; Kellogg, R. M.; Kloosterman, M.; Kaptein, B.; Kamphuis, J.; Shoemaker, H. E. J. Org. Chem. 1990, 55, 5878. (b) Feichter, C.; Faber, K.; Griengl, H. J. Chem. Soc., Perkin Trans. 1 1991, 653. (c) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525. (d) Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643. (f) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365. (g) Pottie, M.; Van der Eycken, J.; Vanewalle, M.; Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319.
9. Resolutions of α,α-disubstituted α-hydroxycarboxylic acid esters have been performed successfully with a series of enzymes: (a) Moorlag, H.; Kellogg, R. M.; Kloosterman, M.; Kaptein, B.; Kamphuis, J.; Shoemaker, H. E. J. Org. Chem. 1990, 55, 5878. (b) Feichter, C.; Faber, K.; Griengl, H. J. Chem. Soc., Perkin Trans. 1 1991, 653. (c) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525. (d) Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643. (f) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365. (g) Pottie, M.; Van der Eycken, J.; Vanewalle, M.; Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319.
10. Resolutions of α,α-disubstituted α-hydroxycarboxylic acid esters have been performed successfully with a series of enzymes: (a) Moorlag, H.; Kellogg, R. M.; Kloosterman, M.; Kaptein, B.; Kamphuis, J.; Shoemaker, H. E. J. Org. Chem. 1990, 55, 5878. (b) Feichter, C.; Faber, K.; Griengl, H. J. Chem. Soc., Perkin Trans. 1 1991, 653. (c) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525. (d) Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643. (f) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365. (g) Pottie, M.; Van der Eycken, J.; Vanewalle, M.; Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319.
11. Resolutions of α,α-disubstituted α-hydroxycarboxylic acid esters have been performed successfully with a series of enzymes: (a) Moorlag, H.; Kellogg, R. M.; Kloosterman, M.; Kaptein, B.; Kamphuis, J.; Shoemaker, H. E. J. Org. Chem. 1990, 55, 5878. (b) Feichter, C.; Faber, K.; Griengl, H. J. Chem. Soc., Perkin Trans. 1 1991, 653. (c) Yee, C.; Blythe, T. A.; McNabb, T. J.; Walts, A. E. J. Org. Chem. 1992, 57, 3525. (d) Sugai, T.; Kakeya, H.; Ohta, H. J. Org. Chem. 1990, 55, 4643. (f) Yang, S.; Hayden, W.; Faber, K.; Griengl, H. Synthesis 1992, 365. (g) Pottie, M.; Van der Eycken, J.; Vanewalle, M.; Dewanckele, J. M.; Röper, H. Tetrahedron Lett. 1989, 30, 5319.
12. For definition and calculation of E see: Chen, C.-H.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
13. Ohta, H.; Miyamae, Y.; Kimura, Y. Chem. Lett. 1989, 379.
14. Ohta, H.; Kimura, Y.; Sugano, Y.; Sugai, T. Tetrahedron 1989, 45, 5469.
15. Cipiciani, A.; Cittadini, M.; Fringuelli, F. Tetrahedron 1988, 54, 7883; and references cited therein.