Systematic Investigation of the Kinetic Resolution of 3-Hydroxy Fatty Acid Esters Using Candida antarctica Lipase B (CALB) and the Influence of Competing Oligomerization on the Enantiomeric Ratios

REFERENCES

• Mori , K. Synthesis of optically active pheromones . Tetrahedron 1989 , 45 , 3233 – 3298 .
   Web of Science ®Google Scholar
• Santaniello , E. ; Ferraboschi , P. ; Grisenti , P. ; Manzocchi , A. The biocatalytic approach to the preparation of enantiomerically pure chiral building blocks . Chem. Rev. 1992 , 92 , 1071 – 1140 .
   Web of Science ®Google Scholar
• de Souza Pereira , R. The use of baker's yeast in the generation of asymmetric centers to produce chiral drugs and other compounds . Crit. Rev. Biotechnol. 1998 , 18 , 25 – 83 .
   PubMed Web of Science ®Google Scholar
• Williams , R. M. ; Cao , J. ; Tsujishima , H. ; Cox , R. J. Asymmetric, stereocontrolled total synthesis of Paraherquamide A . J. Am. Chem. Soc. 2003 , 125 , 12172 – 12178 .
   PubMed Web of Science ®Google Scholar
• Yang , D. ; Gao , Q. ; Zheng , B.-F. ; Zhu , N.-Y. Et2AlCl-promoted asymmetric phenylseleno group transfer radical cyclization reactions of unsaturated β-hydroxy esters. J. Org. Chem. 2004, 69, 8821–8828.
   PubMed Web of Science ®Google Scholar
• Clay , R. J. ; Collom , T. A. ; Karrick , G. L. ; Wemple , J. A safe economical method for the preparation of β-oxo esters . Synthesis 1992 , 290 – 292 .
   Web of Science ®Google Scholar
• Benetti , S. ; Romagnoli , R. ; De Risi , C. ; Spalluto , G. ; Zanirato , V. Mastering β-keto esters . Chem. Rev. 1995 , 95 , 1065 – 1114 .
   Web of Science ®Google Scholar
• Kramer , R. ; Brückner , R. Discrimination of β-ketoesters by ruthenium(II)-binap-catalysed asymmetric hydrogenation . Angew. Chem. Int. Ed. 2007 , 46 , 6537 – 6541 .
   PubMed Web of Science ®Google Scholar
• Kramer , R. ; Brückner , R. Asymmetric hydrogenations one by one: Differentiation of up to three β-ketocarboxylic acid derivatives based on ruthenium(II)-binap catalysis . Chem. Eur. J. 2007 , 13 , 9076 – 9086 .
   PubMed Web of Science ®Google Scholar
• Faber , K. Biotransformations in Organic Chemistry, , 5th ed. ; Springer : Berlin-Heidelberg , 2004 .
   Google Scholar
• Bornscheuer , U. T. ; Kazlauskas , R. J. Hydrolases in Organic Chemistry, , 2nd ed. ; Wiley-VCH : Weinheim , 2006 .
   Google Scholar
• Bornscheuer , U. ; Herar , A. ; Kreye , L. ; Wendel , V. ; Capewell , A. ; Meyer , H. ; Scheper , T. ; Kolisis , F. Factors affecting the lipase catalyzed transesterification reactions of 3-hydroxyesters in organic solvents . Tetrahedron: Asymmetry 1993 , 4 , 1007 – 1016 .
   Web of Science ®Google Scholar
• Capewell , A. ; Wendel , V. ; Bornscheuer , U. ; Meyer , H. H. ; Scheper , T. Lipase-catalysed kinetic resolution of 3-hydroxy esters in organic solvents and supercritical carbon dioxide . Enzyme Microb. Technol. 1996 , 19 , 181 – 186 .
   Web of Science ®Google Scholar
• Ikunaka , M. A process in need is a process indeed: Scalable enantioselective synthesis of chiral compounds for the pharmaceutical industry . Chem. Eur. J. 2003 , 9 , 379 – 388 .
   Web of Science ®Google Scholar
• Garcia , M. J. ; Rebolledo , F. ; Gotor , V. Practical enzymatic route to optically active 3-hydroxyamides: Synthesis of 1,3-aminoalcohols . Tetrahedron: Asymmetry 1993 , 4 , 2199 – 2210 .
   Web of Science ®Google Scholar
• Chen , C. S. ; Shi , C. J. General aspects and optimization of enantioselective biocatalysis in organic solvents: The use of lipases . Angew. Chem. Int. Ed. Engl. 1989 , 28 , 695 – 707 .
   Web of Science ®Google Scholar
• Adam , W. ; Lazarus , M. ; Schmerder , A. ; Humpf , H.-U. ; Saha-Möller , C. R. ; Schreier , P. Synthesis of optically active α-hydroxy acids by kinetic resolution through lipase-catalyzed enantioselective acetylation . Eur. J. Org. Chem. 1998 , 2013 .
   Web of Science ®Google Scholar
• Mezoul , G. ; Lalot , T. ; Brigodiot , M. ; Maréchal , E. Enzyme-catalyzed sythesis of aliphatic polyesters in organic media: Study of transesterification equilibrium shift and characterization of cyclic compounds . J. Polym. Sci. Part A: Polym. Chem. 1995 , 33 , 2691 – 2698 .
   Web of Science ®Google Scholar
• Robinson , G. K. ; Alston , M. J. ; Knowles , C. J. ; Cheetham , P. S. J. ; Motion , K. R. An investigation into the factors influencing lipase-catalyzed intramolecular lactonization in microaqueous systems . Enzyme Microb. Technol. 1994 , 16 , 855 – 863 .
   Web of Science ®Google Scholar
• From , M. ; Adlercreutz , P. ; Mattiasson , B. Lipase-catalyzed esterification of lactic acid . Biotechnol. Lett. 1997 , 19 , 315 – 317 .
   Web of Science ®Google Scholar
• Fischer , P. ; Heitzer , W. ; Thielacker , R. Präparatives Praktikum für chemisch-technische Assistenten ; Thieme : Stuttgart , 1988 .
   Google Scholar
• Clay , R. J. ; Collom , T. A. ; Karrick , G. L. ; Wemple , J. A safe economical method for the preparation of β-oxo esters . Synthesis 1992 , 290 – 292 .
   Web of Science ®Google Scholar