Ruthenium- and lipase-catalyzed inversion of l-lactates

Tetrahedron Letters

Volumn 53, Issue 47, 2012, Pages 6326-6328

  Shuklov, Ivan A ^a   Dubrovina, Natalia V ^a   Schulze, Joachim ^b   Tietz, Wolfgang ^b   Kühlein, Klaus ^c   Börner, Armin ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b UHDE GMBH   (Germany)

^c Fasanenstr 41   (Germany)

Author keywords

Inversion; Lactate; Lipase; Ruthenium; Stereoisomers

Indexed keywords

LACTIC ACID; RUTHENIUM; SODIUM CARBONATE; TRIACYLGLYCEROL LIPASE;

ACETYLATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL MODIFICATION; COLUMN CHROMATOGRAPHY; ENANTIOSELECTIVITY; INVERSION; RACEMIZATION; STEREOCHEMISTRY; TEMPERATURE;

EID: 84867858496     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.08.126     Document Type: Article

References (43)

1. D. Garlotta J. Polym. Environ. 9 2001 63 84
2. R. Gattin, A. Copinet, C. Bertrand, and Y. Couturier J. Polym. Environ. 9 2001 11 17
3. K. Numata, R.K. Srivastava, A. Finne-Wistrand, A.-C. Albertsson, Y. Doi, and H. Abe Biomacromolecules 8 2007 3115 3125
4. H.-J. Endres, and A. Siebert-Raths Technische Biopolymere 2009 München Hanser p. 293
5. R. Auras, L.-T. Lim, S.E. M. Selke, and H. Tsuji Poly(Lactic Acid), Synthesis, Structures, Properties, Processing and Application 2010 Wiley Hoboken
6. J.W. Leenslag, and A. Pennings J. Makromol. Chem. 188 1987 1809 1814
7. A. Kowalski, A. Duda, and S. Penczek Macromolecules 31 1998 2114 2122
8. H.R. Kricheldorf, I. Kreiser-Saunders, and A. Stricker Macromolecules 33 2000 702 709
9. K.M. Stridsberg, M. Ryner, and A.C. Albertsson Adv. Polym. Sci. 157 2002 41 65
10. A.P. Gupta, and V. Kumar Eur. Polym. Mater. 43 2007 4053 4074
11. M. Baśko, and P. Kubisa J. Polym. Sci., A: Polym. Chem. 48 2010 2650 2658
12. Nonokawa, R, Jpn. Pat. JP 2,012,001,619, 2012; Chem. Abstr. 2012, 156, 100144.
13. J.-C. Buffet, A. Martin, M. Kol, and J. Okuda Polym. Chem. 2011 2378 2384
14. J.-C. Buffet, J.P. Davin, T.P. Spaniol, and J. Okuda New J. Chem. 35 2011 2253 2257
15. For example since 2007 BASF sells PLA-blend under the trade name Ecovio®: http://www.plasticsportal.net/wa/plasticsEU~de-DE/portal/show/ content/literature/ecovio.
16. Nakanishi, N.; Tokuda, H.; Honma, H.; Suzuki, M. Jpn. Pat. JP 2,011,200,161, 2011; Chem. Abstr. 2011, 155, 508088.
17. Hong, C. H.; Han, D. S. Ger. Pat. DE 1,020,100,311,52, 2011; Chem. Abstr. 2011, 155, 533916.
18. Josha, M.; Nakai, T.; Nakagawa, A.; Suzuki, T. Jpn. Pat. JP 2,011,092,045, 2011; Chem. Abstr. 2011, 154, 563384.
19. A. Trontel, A. Batusic, I. Gusic, A. Slavica, B. Santek, and S. Novak Food Tech. Biotechnol. 49 2011 75 82
20. Y. Tashiro, W. Kaneko, Y. Sun, K. Shibata, K. Inokuma, T. Zendo, and K. Sonomoto Appl. Microbiol. Biotechnol. 89 2011 1741 1750
21. B. Schäffner, V. Andrushko, S.P. Verevkin, J. Holz, and A. Börner ChemSusChem 1 2008 934 940
22. I. Shuklov, H. Jiao, J. Schulze, W. Tietz, K. Kühlein, and A. Börner Tetrahedron Lett. 52 2011 1027 1030
23. G. Cainelli, F. Manescalchi, G. Martelli, M. Panunzio, and L. Plessi Tetrahedron Lett. 26 1985 3369 3372
24. R.W. Feenstra, E.H.M. Stokkingreef, R.J.F. Nivard, and H.C.J. Ottenheijm Tetrahedron 44 1988 5583 5595
25. M. Schürch, T. Heinz, R. Aeschimann, T. Mallat, A. Pfaltz, and A. Baiker J. Catal. 173 1998 187 195
26. T. Heinz, G. Wang, A. Pfaltz, B. Minder, M. Schuerch, T. Mallat, and A. Baiker J. Chem. Soc., Chem. Commun. 1995 1421 1422
27. M. Garland, and H.U. Blaser J. Am. Chem. Soc. 112 1990 7048 7050
28. A.B. Charette, M.K. Janes, and A.A. Boezio J. Org. Chem. 66 2001 2178 2180
29. T.Y.S. But, and P.H. Toy J. Am. Chem. Soc. 128 2006 9636 9637
30. B.H. Lipshutz, D.W. Chung, B. Rich, and R. Corral Org. Lett. 8 2006 5069 5072
31. B.A. Persson, F.F. Huerta, and J.-E. Bäckvall J. Org. Chem. 64 1999 5237 5249
32. J.H. Choi, Y.H. Kim, S.H. Nam, S.T. Shin, M.-J. Kim, and J. Park Angew. Chem., Int. Ed. 41 2002 2373 2376
33. J.H. Choi, Y.K. Choi, Y.H. Kim, E.S. Park, E.J. Kim, M.-J. Kim, and J. Park J. Org. Chem. 69 2004 1972 1977
34. A.L.E. Larsson, B.A. Persson, and J.-E. Bäckvall Angew. Chem., Int. Ed. 36 1997 1211 1212
35. B. Martin-Matute, M. Edin, K. Bogar, F.B. Kaynak, and J.-E. Bäckvall J. Am. Chem. Soc. 127 2005 8817 8825
36. B.M. Trost, and F.D. Toste J. Am. Chem. Soc. 125 10 2003 3090 3100
37. F.F. Huerta, Y.R.S. Laxmi, and J.-E. Bäckvall Org. Lett. 2000 1037 1040
38. M. Edin, B. Martin-Matute, and J.-E. Bäckvall Tetrahedron: Asymmetry 17 2006 708 715
39. B.L. Conley, M.K. Pennington-Boggio, E. Boz, and T. Williams J. Chem. Rev. 110 2010 2294 2312
40. Y. Shvo, D. Czarkie, and Y. Rahamim J. Am. Chem. Soc. 108 1986 7400 7402
41. Y.S. Lee, J.H. Hong, N.Y. Jeon, K. Won, and B.T. Kim Org. Proc. Res. Dev. 8 2004 948 951
42. J. Paetzold, and J.E. Bäckvall J. Am. Chem. Soc. 127 2005 17620 17621
43. The optical purity of the product was determined by chiral GC (Lipodex E) of the corresponding bis-trifluoroacetate derivative.