Exploration of chiral induction on epoxides in lipase-catalyzed epoxidation of alkenes using (2R,3S,4R,5S)-(–)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate

Add time:09/05/2019    Source:sciencedirect.com

Epoxidation of alkenes by peracid, generated in situ from (2R,3S,4R,5S)-(−)-2,3:4,6-di-O-isopropylidiene-2-keto-l-gulonic acid monohydrate [(−)-DIKGA] and hydrogen peroxide by lipase catalysis induces chirality on the product epoxides with moderate to good enantioselectivity (35–71%). Alkoxy/aralkyloxy styrenes however did not undergo any epoxidation. (R)-(+)-4-Hydroxy styrene-7,8-oxide was formed and isolated with moderate enantiomeric excess (57%) but was found to have poor stability.

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