Recent developments in the asymmetric hydrolytic ring opening of epoxides catalysed by microbial epoxide hydrolase

Biocatalysis as an alternative for the production of chiral epoxides: A comparative review

“…An attractive alternative to the Jacobson's HKR reaction is the use of EHs, which are readily available from a wide range of microorganism sources in sufficient quantities, and the large enzyme reservoir provides feasible tools to meet the potential requirements of synthetic chemists [24,147]. Currently, the kinetic resolution of racemic epoxides by EH has been well developed, and excellent enantioselectivity has been achieved for a variety of substrates (Fig.…”

“…Several reviews on the preparation of chiral epoxides have been published [3,7,8,[22][23][24][25][26]. This review does not seek to provide a comprehensive list of all kinds of synthetic/enzymatic methods, but rather to emphasize the potential of biocatalysis in the preparation of chiral epoxides.…”

“…Functioned as catalyzing the kinetic resolution and the enantioconvergent hydrolysis of racemic epoxides into the corresponding diols, the enzyme has been intensively explored in the past decades, and a number of excellent reviews focusing on its application in organic synthesis have been published [24,[131][132][133]. The cofactor-independent EH catalysis has several advantages, such as the broad substrate specificities with high regio-and enantioselectivity and activity in organic solvents, which leads to many successful applications [132].…”

“…Since the nucleophile can attack both carbon atoms of the epoxide ring, the reaction would proceed in four possible pathways (k 1 -k 4 , Scheme 11) [24,131]. The absolute configuration of the product is a result of both the enantioselectivity and the regioselectivity of the reaction, which depends on the enzyme origin and the nature of the substituent on the epoxide ring.…”

“…Therefore, enantioconvergent processes are possible for EH-catalyzed reactions. In case of mono-substituted epoxides, it is common that the enantioconvergent reactions proceed via both the k 1 and k 4 pathways, leading to the (R)-diol in 100% theoretical yield [24,132,138].…”