56374-24-4Relevant articles and documents
Microbiological transformations 43. Epoxide hydrolases as tools for the synthesis of enantiopure α-methylstyrene oxides: A new and efficient synthesis of (S)-ibuprofen
Cleij,Archelas,Furstoss
, p. 5029 - 5035 (2007/10/03)
Biohydrolysis of various α-methylstyrene oxide derivatives, differently substituted at the aromatic ring, was investigated using 10 epoxide hydrolases from different origins. Our results indicate that the enantioselectivity of these biohydrolyses strongly depends on the nature of the enzyme and of the substituent. Using some of these enzymes, this approach allows to prepare these epoxides in high optical purity. The potentiality to perform efficient preparative-scale resolution using such a biocatalyst was illustrated by the four-step synthesis of (S)-ibuprofen, a nonsteroidal antiinflammatory drug and household pain killer, one of the top-ten drugs sold worldwide. Using a combined chemoenzymatic strategy, we were thus able to set up a four-step enantioconvergent procedure allowing for the synthesis of this compound in optically pure form and with a 47% overall yield, including the resolution process, due to a possible recycling of the formed diol via chemical racemisation.
Enantioselective hydrolysis of 2,2-disubstituted oxiranes mediated by microsomal epoxide hydrolase
Basavaiah,Bhaskar Raju
, p. 3293 - 3306 (2007/10/03)
2-Aryl-2-methyloxiranes are enantioselectively hydrolyzed with microsomal epoxide hydrolase from pig liver to provide 1,2-diols containing a tertiary benzylic alcohol stereogenic centre upto 34% enantiomeric purities.
