Efficient Lipase-Catalyzed Kinetic Resolution and Dynamic Kinetic Resolution of β-Hydroxy Nitriles. Correction of Absolute Configuration and Transformation to Chiral β-Hydroxy Acids and γ-Amino Alcohols

Advanced Synthesis and Catalysis

Volumn 344, Issue 9, 2002, Pages 947-952

  Pàmies, Oscar ^a   Bäckvall, Jan E ^a  

^a STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

hydroxy acids; amino alcohols; Dynamic kinetic resolution; Kinetic resolution; Ruthenium

Indexed keywords

EID: 19044384195     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/1615-4169(200210)344:9<947::AID-ADSC947>3.0.CO;2-Z     Document Type: Review

References (27)

1. For recent reviews on DKR, see: a) M. T. El Gihani, J. M. J. Williams, Curr. Opin. Chem. Biol. 1999, 3, 11; b) U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999, 10, 107; c) R. Azerad, D. Buisson, Curr. Opin. Biotechnol. 2000, 77, 565; d) F. F. Huerta, A. B. E. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321.
2. For recent reviews on DKR, see: a) M. T. El Gihani, J. M. J. Williams, Curr. Opin. Chem. Biol. 1999, 3, 11; b) U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999, 10, 107; c) R. Azerad, D. Buisson, Curr. Opin. Biotechnol. 2000, 77, 565; d) F. F. Huerta, A. B. E. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321.
3. For recent reviews on DKR, see: a) M. T. El Gihani, J. M. J. Williams, Curr. Opin. Chem. Biol. 1999, 3, 11; b) U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999, 10, 107; c) R. Azerad, D. Buisson, Curr. Opin. Biotechnol. 2000, 77, 565; d) F. F. Huerta, A. B. E. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321.
4. For recent reviews on DKR, see: a) M. T. El Gihani, J. M. J. Williams, Curr. Opin. Chem. Biol. 1999, 3, 11; b) U. T. Strauss, U. Felfer, K. Faber, Tetrahedron: Asymmetry 1999, 10, 107; c) R. Azerad, D. Buisson, Curr. Opin. Biotechnol. 2000, 77, 565; d) F. F. Huerta, A. B. E. Minidis, J.-E. Bäckvall, Chem. Soc. Rev. 2001, 30, 321.
5. rd ed., Springer, Graz, Austria, 1996.
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8. See for instance: a) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835; b) C. P. Kordik, A. B. Reitz, J. Med. Chem. 1999, 42, 181; c) L. A. Paquette, T. Z. Wang, E. Pinard, J. Am. Chem. Soc. 1995, 117, 1455; d) H. Xiaojun, E. J. Corey, Org. Lett. 2000, 2, 2543.
9. See for instance: a) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835; b) C. P. Kordik, A. B. Reitz, J. Med. Chem. 1999, 42, 181; c) L. A. Paquette, T. Z. Wang, E. Pinard, J. Am. Chem. Soc. 1995, 117, 1455; d) H. Xiaojun, E. J. Corey, Org. Lett. 2000, 2, 2543.
10. See for instance: a) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835; b) C. P. Kordik, A. B. Reitz, J. Med. Chem. 1999, 42, 181; c) L. A. Paquette, T. Z. Wang, E. Pinard, J. Am. Chem. Soc. 1995, 117, 1455; d) H. Xiaojun, E. J. Corey, Org. Lett. 2000, 2, 2543.
11. See for instance: a) D. J. Ager, I. Prakash, D. R. Schaad, Chem. Rev. 1996, 96, 835; b) C. P. Kordik, A. B. Reitz, J. Med. Chem. 1999, 42, 181; c) L. A. Paquette, T. Z. Wang, E. Pinard, J. Am. Chem. Soc. 1995, 117, 1455; d) H. Xiaojun, E. J. Corey, Org. Lett. 2000, 2, 2543.
12. a) F. F. Huerta, Y. R. S. Laxmi, J. E. Bäckvall, Org. Lett. 2000, 2, 1037;
13. b) F. F. Huerta, J. E. Bäckvall, Org. Lett. 2001, 3, 1209;
14. c) O. Pàmies, J.-E. Bäckvall, J. Org. Chem. 2001, 66, 4022;
15. d) O. Pàmies, J.-E. Bäckvall, Adv. Synth. Catal. 2001, 343, 726;
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17. f) A.-B. L. Runmo, O. Pàmies, K. Faber, J.-E. Bäckvall, Tetrahedron Lett. 2002, 43, 2983.
18. Our assignment was based on the reported sign of the (R)-2-cyano-1-phenylethyl acetate: T. Itoh, K. Mitsukura, W. Kanphai, Y. Takagi, H. Kihara, H. Tsukube, J. Org.Chem. 1997, 62, 9165. Unfortunately, this turned out to be in error.
19. [5d]
20. Further decrease of the amount of enzyme gives slightly better enantioselectivity, but with lower conversions.
21. This indicates that the enzyme is denatured under the DKR conditions.
22. A similar procedure has been used in the practical synthesis of different enantiomerically pure acetamides, see: O. Pàmies, A. H. Éll, J. S. M. Samec, N. Hermanns, J.-E. Bäckvall, Tetrahedron Lett. 2002, 43, 4699.
23. D. Mitchell, T. M. Koenig, Synth. Commun. 1995, 25, 1231.
24. (S)-3-Hydroxy-3-phenylpropanoic acid product sheet from Fluka Chemie AG, Switzerland.
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26. J. R. Dehli, V. Gotor, Tetrahedron: Asymmetry 2000, 11, 3693.
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