Chemoenzymatic enantioselective synthesis of 2-substituted glycerol derivatives

Tetrahedron Asymmetry

Volumn 23, Issue 6-7, 2012, Pages 428-433

  Bolduc, Mélanie ^a   Bergeron, Jérôme ^a   Michaud, Annie ^a   Pelchat, Nicholas ^a   Morin, Pierre ^a   Dasser, Mohammed ^b   Chênevert, Robert ^a  

^a UNIVERSITÉ LAVAL   (Canada)

^b OmegaChem   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL ENZYME; BUTYRIC ACID; GLYCEROL DERIVATIVE; LIPASE B; TRIACYLGLYCEROL LIPASE;

ACYLATION; ARTICLE; BIOCATALYST; BURKHOLDERIA CEPACIA; CANDIDA ANTARCTICA; ENANTIOSELECTIVITY; NONHUMAN; PRIORITY JOURNAL; RHIZOPUS;

EID: 84861024235     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2012.04.001     Document Type: Article

References (40)

1. A. Dibenedetto, A. Angelini, M. Aresta, J. Ethiraj, C. Fragale, and F. Nocito Tetrahedron 67 2011 1308 1313
2. J.I. Garcia, H. Garcia-Marin, J.A. Mayoral, and P. Perez Green Chem. 12 2010 426 434
3. Y. Gu, and F. Jérôme Green Chem. 12 2010 1127 1138
4. C.H. Zhou, J.N. Beltramini, Y.X. Fan, and G.Q. Lu Chem. Soc. Rev. 37 2008 527 549
5. A. Behr, J. Eilting, K. Irawadi, J. Leschinski, and F. Lindner Green Chem. 10 2008 13 30
6. M. Pagliaro, R. Ciriminna, H. Kimura, M. Rossi, and C. Della Pina Angew. Chem., Int. Ed. 46 2007 4434 4440
7. R. Kourist, and U.T. Bornscheuer Appl. Microbiol. Biotechnol. 91 2011 505 517
8. D. Seebach Angew. Chem., Int. Ed. 50 2011 96 101
9. J.L. Stymiest, V. Bagutski, R.M. French, and V.K. Aggarwal Nature 456 2008 778 783
10. P.G. Cozzi, R. Hilgraf, and N. Zimmermann Eur. J. Org. Chem. 2007 5969 5994
11. J. Christoffers, and A. Baro Quaternary Stereocenters, Challenges and Solutions for Organic Synthesis 2005 Wiley-VCH Weinheim
12. I. Denissova, and L. Barriault Tetrahedron 59 2003 10105 10146
13. E.J. Corey, and A. Guzman-Perez Angew. Chem., Int. Ed. 37 1998 388 401
14. S. Sano, T. Tsumura, N. Tanimoto, T. Honjo, M. Nakao, and Y. Nagao Synlett 2010 256 260
15. B. Jung, and S.H. Kang Proc. Natl. Acad. Sci. U.S.A. 104 2007 1471 1475
16. B. Jung, M.S. Hong, and S.H. Kang Angew. Chem., Int. Ed. 46 2007 2616 2618
17. T. Harada, H. Nakajima, T. Ohnishi, M. Takeuchi, and A. Oku J. Org. Chem. 57 1992 720 724
18. R. Chênevert, G. Courchesne, and N. Pelchat Bioorg. Med. Chem. 14 2006 5389 5396
19. R. Chênevert, D. Duguay, F. Touraille, and D. Caron Tetrahedron: Asymmetry 15 2004 863 866
20. R. Chênevert, M. Simard, J. Bergeron, and M. Dasser Tetrahedron: Asymmetry 15 2004 1889 1892
21. R. Chênevert, and D. Caron Tetrahedron: Asymmetry 13 2002 339 342
22. S.T. Chen, and J.M. Fang J. Org. Chem. 62 1997 4349 4357
23. R.P. Hof, and R.M. Kellogg J. Org. Chem. 61 1996 3423 3427
24. B. Wirz, R. Barner, and J. Hübscher J. Org. Chem. 58 1993 3980 3984
25. N. Watanabe, T. Sugai, and H. Ohta Chem. Lett. 1992 657 660
26. M. Sodeoka, H. Yamada, and M. Shibasaki J. Am. Chem. Soc. 112 1990 4906 4911
27. E.J.T. Chrystal, A.H. Haines, and R. Patel Carbohydr. Res. 186 1989 320 325
28. C.J. Sih, and S.H. Wu Resolution of Enantiomers via Biocatalysis E.L. Eliel, S.H. Wilen, N.L. Allinger, Topics in Stereochemistry Vol. 19 1989 Wiley New York 63 125
29. For a website see: http://www.orgc.tugraz.at/ (by Faber, K.; Hönig, H.; Kleewein, A., 2006).
30. R. Chênevert, C. Lévesque, and P. Morin J. Org. Chem. 73 2008 9501 9503
31. R. Chênevert, F. Jacques, P. Giguère, and M. Dasser Tetrahedron: Asymmetry 19 2008 1333 1338
32. B. Morgan, D.R. Dodds, A. Zaks, D.R. Andrews, and R.J. Kleese J. Org. Chem. 62 1997 7736 7743
33. C. Monneret, and J.C. Florent Synlett 1994 305 318
34. B.S. Jeong, J.W. Lee, H.J. Son, B.Y. Kim, and S.K. Ahn Tetrahedron: Asymmetry 16 2005 3795 3801
35. U.T. Bornscheuer, and R.J. Kazlauskas Hydrolase in Organic Chemistry 2006 Wiley-VCH Weinheim pp 113-116
36. G.A. Kraus, and A. Kempema Synthesis 2010 389 391
37. Z. You, A.H. Hoveyda, and M.L. Snapper Angew. Chem., Int. Ed. 48 2009 547 550
38. A. Avenoza, C. Cativiela, J.M. Peregrina, D. Sucunza, and M.M. Zurbano Tetrahedron: Asymmetry 12 2001 1383 1388
39. K.J. Hale, S. Manaviazar, and S.A. Peak Tetrahedron Lett. 35 1994 425 428
40. J.C. Florent, J. Ughetto-Monfrin, and C. Monneret J. Org. Chem. 52 1987 1051 1056