Chemoenzymatic method for the preparation of γ-amino alcohols from phenylfuran-based aldehydes; lipase-catalyzed kinetic resolution of β-hydroxy nitriles

Tetrahedron Asymmetry

Volumn 21, Issue 6, 2010, Pages 739-745

  Turcu, Mihaela C ^a   Perkiö, Päivi ^a   Kanerva, Liisa T ^a  

^a UNIVERSITY OF TURKU   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE DERIVATIVE; AMINOALCOHOL; BETA HYDROXY NITRILE; ESTER DERIVATIVE; FURAN DERIVATIVE; GAMMA AMINO ALCOHOL; NITRILE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ALCOHOLYSIS; ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DEPROTECTION REACTION; DRUG PURIFICATION; DRUG SYNTHESIS; ENANTIOMER; ENZYME MECHANISM; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY; THERMOMONOSPORA; THERMOMYCES LANUGINOSUS;

EID: 77953326380     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.04.025     Document Type: Article

References (32)

1. Bergmeier S.C. Tetrahedron 56 (2000) 2561-2576
2. Lundell K., and Kanerva L.T. Chim. Oggi/Chem. Today 25 (2007) 26-30
3. Wong D.T., Horng J.S., Bymaster F.P., Hauser K.L., and Molloy B.B. Life Sci. 15 (1974) 471-479
4. Sahu P.K., Wang C.-H., and Lee S.-L. J. Phys. Chem. B 113 (2009) 14529-14535
5. Simpson D., and Plosker G.L. CNS Drugs 18 (2004) 397-401
6. Bymaster F.P., Beedle E.E., Findlay J., Gallagher P.T., Krushinski J.H., Mitchell S., Robertson D.W., Thompson D.C., Wallace L., and Wong D.T. Bioorg. Med. Chem. Lett. 13 (2003) 4477-4480
7. Ohkuma T., Koizumi M., Yoshida M., and Noyori R. Org. Lett. 2 (2000) 1749-1751
8. Liu D., Gao W., Wang C., and Zhang X. Angew. Chem., Int. Ed. 44 (2005) 1687-1689
9. Suto Y., Tsuji R., Kanai M., and Shibasaki M. Org. Lett. 7 (2005) 3757-3760
10. Granander J., Eriksson J., and Hilmersson G. Tetrahedron: Asymmetry 17 (2006) 2021-2027
11. Mun S., Lee J.-E., and Yun J. Org. Lett. 8 (2006) 4887-4889
12. Liu P.N., Gu P.M., Wang F., and Tu Y.Q. Org. Lett. 6 (2004) 169-172
13. Hammond R.J., Poston B.W., Ghiviriga I., and Feske B.D. Tetrahedron Lett. 48 (2007) 1217-1219
14. Ankati H., Zhu D., Yang Y., Biehl E.R., and Hua L. J. Org. Chem. 74 (2009) 1658-1662
15. Kamal A., Ramesh Khanna G.B., and Ramu R. Tetrahedron: Asymmetry 13 (2002) 2039-2051
16. Kamal A., Ramesh Khanna G.B., Krishnaji T., and Ramu R. Bioorg. Med. Chem. Lett. 15 (2005) 613-615
17. Kamal A., Ramesh Khanna G.B., Krishnaji T., Tekumalla V., and Ramu R. Tetrahedron: Asymmetry 16 (2005) 1485-1494
18. Pàmies O., and Bäckvall J.-E. Adv. Synth. Catal. 344 (2002) 947-952
19. Turcu M.C., Perkiö P., and Kanerva L.T. Arkivoc (2009) 251-263
20. Itoh T., Takagi Y., and Nishiyama S. J. Org. Chem. 56 (1991) 1521-1524
21. Kanerva L.T., Kosonen M., Vänttinen E., Huuhtanen T.T., and Dahlqvist M. Acta Chem. Scand. 46 (1992) 1101-1105
22. Lundell K., Lehtinen P., and Kanerva L.T. Adv. Synth. Catal. 345 (2003) 790-796
23. Torre O., Gotor-Fernández V., and Gotor V. Tetrahedron: Asymmetry 17 (2006) 860-866
24. Kawano Y., Kaneko N., and Mukaiyama T. Chem. Lett. 34 (2005) 1508-1509
25. Vänttinen E., and Kanerva L.T. Tetrahedron: Asymmetry 8 (1997) 923-933
26. Martinelle M., and Hult K. Biochim. Biophys. Acta 1251 (1995) 191-197
27. García-Alles L.F., and Gotor V. Biotechnol. Bioeng. 59 (1998) 163-170
28. Ganem B., and Osby J.O. Chem. Rev. 86 (1986) 763-780
29. Caddick S., De K. Haynes A.K., Judd D.B., and Williams M.R.V. Tetrahedron Lett. 41 (2000) 3513-3516
30. Caddick S., Judd D.B., De K. Lewis A.K., Reich M.T., and Williams M.R.V. Tetrahedron 59 (2003) 5417-5423
31. Kanerva L.T., and Sundholm O. J. Chem. Soc., Perkin. Trans. 1 (1993) 2407-2410
32. Chen C.-S., Fujimoto Y., Girdaukas G., and Sih C.J. J. Am. Chem. Soc. 104 (1982) 7294