Lipase-catalyzed asymmetric acylation in the chemoenzymatic synthesis of furan-based alcohols

Tetrahedron Asymmetry

Volumn 24, Issue 2-3, 2013, Pages 142-150

  Hara, Piia ^a   Turcu, Mihaela Claudia ^a   Sundell, Riku ^a   Toşa, Monica ^b   Paizs, Csaba ^b   Irimie, Florin Dan ^b   Kanerva, Liisa T ^a  

^a UNIVERSITY OF TURKU   (Finland)

^b BABE BOLYAI UNIVERSITY   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; ALCOHOL DERIVATIVE; CARBONYL DERIVATIVE; DIISOPROPYL ETHER; FURAN DERIVATIVE; LIPASE B; METHANOL; VINYL ACETATE; WATER;

ACYLATION; ALCOHOLYSIS; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; DEPROTECTION REACTION; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME KINETICS; HYDROLYSIS; PRIORITY JOURNAL; RACEMIC MIXTURE; SYNTHESIS;

EID: 84873619669     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.11.016     Document Type: Article

References (28)

1. B.H. Lipshutz Chem. Rev. 86 1986 795 819
2. G. Piancatelli, M. D'Auria, and F. D'Onofrio Synthesis 1994 867 888
3. S.F. Martin, and P.W. Zinke J. Org. Chem. 56 1991 6600 6606
4. D. Balachari, and G.A. O'Doherty Org. Lett. 2 2000 863 866
5. A. Boto, D. Hernández, and R. Hernández Org. Lett. 9 2007 1721 1724
6. P. Traxler, J. Gruner, and J.A.L. Auden J. Antibiot. 30 1977 289 296
7. L. Cipolla, A. Polissi, C. Airoldi, L. Gabrielli, S. Merlo, and F. Nicotra Curr. Med. Chem. 18 2011 830 852
8. Kanerva, L. T., Liljeblad, A. in Encyclopedia of Catalysis: Transesterification - Biological, Wiley Online Library, 2010; doi: http://dx.doi.org/10.1002/0471227617.eoc197.
9. C. Paizs, M. Toşa, V. Bódai, I. Szakács, I. Kmecz, B. Simándi, C. Majdik, L. Novák, F.-D. Irimie, and L. Poppe Tetrahedron: Asymmetry 14 2003 1943 1949
10. C. Paizs, P. Tähtinen, K. Lundell, L. Poppe, F.-D.T. Irimie, and L. Irimie Tetrahedron: Asymmetry 14 2003 1895 1904
11. J. Brem, C. Paizs, M.I. Toşa, E. Vass, and F.-D. Irimie Tetrahedron: Asymmetry 20 2009 489 496
12. J. Brem, A. Liljeblad, C. Paizs, M.I. Toşa, F.-D. Irimie, and L.T. Kanerva Tetrahedron: Asymmetry 22 2011 315 322
13. M.C. Turcu, P. Perkiö, and L.T. Kanerva Tetrahedron: Asymmetry 21 2010 739 745
14. R.J. Kazlauskas, A.N.E. Weissfloch, A.T. Rappaport, and L.A. Cuccia J. Org. Chem. 56 1991 2656 2665
15. J. Kaminska, I. Górnicka, M. Sikora, and J. Góra Tetrahedron: Asymmetry 7 1996 907 910
16. B.A. Persson, A.L.E. Larsson, M. Le Ray, and J.-E. Bäckvall J. Am. Chem. Soc. 121 1999 1645 1650
17. M. Päiviö, D. Mavrynsky, R. Leino, and L.T. Kanerva Eur. J. Org. Chem. 2011 1452 1457
18. D. Rotticci, F. Hffner, C. Orrenius, T. Norin, and K. Hult J. Mol. Catal. B: Enzymat. 5 1998 267 272
19. C.-S. Chen, Y. Fujimoto, G. Girdaukas, and C.J. Sih J. Am. Chem. Soc. 104 1982 7294 7299
20. A. Liljeblad, H.-M. Kavenius, P. Tähtinen, and L.T. Kanerva Tetrahedron: Asymmetry 18 2007 181 191
21. X.-G. Li, M. Rantapaju, and L.T. Kanerva Eur. J. Org. Chem. 2011 1744 1762
22. See for instance H.K. Weber, H. Weber, and R.J. Kazlauskas Tetrahedron: Asymmetry 10 1999 2635 2638
23. Z.Cs. Gyarmati, A. Liljeblad, G. Argay, A. Kálmán, G. Bernáth, and L.T. Kanerva Adv. Synth. Catal. 346 2004 566 572
24. L. Veum, L.T. Kanerva, P.J. Halling, T. Maschmeyer, and U. Hanefeld Adv. Synth. Catal. 347 2005 1015 1021
25. A. K. Hult, and P. Berglund Trends Biotechnol. 25 2007 231 238
26. M. Kapoor, and M.N. Gupta Process Biochem. 47 2012 555 569
27. L.C. Bencze, C. Paizs, M. Toşa, and F.-D. Irimie Tetrahedron: Asymmetry. 21 2010 356 364
28. H. Meerwein, E. Buchner, and K. Emster J. Prakt. Chem. 152 1939 237