Dynamic kinetic resolution: Synthesis of optically active α-amino acid derivatives

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1687-1690

  Brown, Stuart A ^a   Parker, Marie Claire ^b   Turner, Nicholas J ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; ALPHA AMINO ACID; BASE; FUNGAL ENZYME; OXAZOLONE; SOLVENT; TRIACYLGLYCEROL LIPASE;

ARTICLE; CANDIDA ANTARCTICA; CATALYST; CHEMICAL REACTION KINETICS; ENANTIOMER; NONHUMAN; OPTICAL ROTATION; PRIORITY JOURNAL; RACEMIC MIXTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0034607765     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00108-7     Document Type: Article

References (14)

1. Faber, K. Lipases. In Biotransformations in Organic Chemistry; Springer-Verlag, 1995; pp. 80-105.
2. For recent reviews on DKR, see: Noyori, R.; Tokungaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56; Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475-1490; Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447-456.
3. For recent reviews on DKR, see: Noyori, R.; Tokungaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56; Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475-1490; Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447-456.
4. For recent reviews on DKR, see: Noyori, R.; Tokungaga, M.; Kitamura, M. Bull. Chem. Soc. Jpn. 1995, 68, 36-56; Ward, R. S. Tetrahedron: Asymmetry 1995, 6, 1475-1490; Caddick, S.; Jenkins, K. Chem. Soc. Rev. 1996, 447-456.
5. Turner, N. J.; Winterman, J. R.; McCague, R.; Parratt, J. S.; Taylor, S. J. C. Tetrahedron Lett. 1995, 36, 1113-1116.
6. Bevinakatti, H. S.; Newadkar, R. V.; Banerji, A. A. J. Chem. Soc., Chem. Commun. 1990, 1091; Bevinakatti, H. S.; Banerji, A. A.; Newadkar, R. V.; Mokashi, A. Tetrahedron: Asymmetry 1992, 3, 1505; Gu, R.-L.; Lee, I. S.; Sih, C. J. Tetrahedron Lett., 1992, 33, 1953; Crich, J.; Brieva, R.; Marquart, P.; Gu, R.-L.; Flemming, S.; Sih, C. J. J. Org. Chem. 1993, 58, 3252.
7. Bevinakatti, H. S.; Newadkar, R. V.; Banerji, A. A. J. Chem. Soc., Chem. Commun. 1990, 1091; Bevinakatti, H. S.; Banerji, A. A.; Newadkar, R. V.; Mokashi, A. Tetrahedron: Asymmetry 1992, 3, 1505; Gu, R.-L.; Lee, I. S.; Sih, C. J. Tetrahedron Lett., 1992, 33, 1953; Crich, J.; Brieva, R.; Marquart, P.; Gu, R.-L.; Flemming, S.; Sih, C. J. J. Org. Chem. 1993, 58, 3252.
8. Bevinakatti, H. S.; Newadkar, R. V.; Banerji, A. A. J. Chem. Soc., Chem. Commun. 1990, 1091; Bevinakatti, H. S.; Banerji, A. A.; Newadkar, R. V.; Mokashi, A. Tetrahedron: Asymmetry 1992, 3, 1505; Gu, R.-L.; Lee, I. S.; Sih, C. J. Tetrahedron Lett., 1992, 33, 1953; Crich, J.; Brieva, R.; Marquart, P.; Gu, R.-L.; Flemming, S.; Sih, C. J. J. Org. Chem. 1993, 58, 3252.
9. Bevinakatti, H. S.; Newadkar, R. V.; Banerji, A. A. J. Chem. Soc., Chem. Commun. 1990, 1091; Bevinakatti, H. S.; Banerji, A. A.; Newadkar, R. V.; Mokashi, A. Tetrahedron: Asymmetry 1992, 3, 1505; Gu, R.-L.; Lee, I. S.; Sih, C. J. Tetrahedron Lett., 1992, 33, 1953; Crich, J.; Brieva, R.; Marquart, P.; Gu, R.-L.; Flemming, S.; Sih, C. J. J. Org. Chem. 1993, 58, 3252.
10. de Jersey, J.; Zerner, B. Biochemistry 1969, 8, 1967.
11. Winterman, J. R. PhD thesis; Chemo-Enzymic Methods for the Synthesis of Optically Active α-Amino Acids; University of Exeter, 1996.
12. 3N (0.25 equiv., optional) and lipase (100 mg). The flask was stoppered and placed in an orbital incubator at 37°C and the reaction monitored by TLC. Upon consumption of the starting material the lipase was filtered off and washed with solvent (2×10 mL). The combined organic fractions were evaporated under reduced pressure and the crude product purified by column chromatography to give the desired product as a colourless solid. In all cases the (S)-isomer of the product predominated.
13. Brown, S. A.; Parker, M.-C.; Robertson, L.; Turner, N. J. J. Chem. Soc., Chem. Commun. 1998, 2247.
14. Maugard, T.; Remaud-Simeon, M.; Petre, D.; Monsan, P. Tetrahedron 1997, 53, 7587-7594.