Selectivity enhancement of epoxide hydrolase catalyzed resolution of 2, 2-disubstituted oxiranes by substrate modification

I Osprian, W Stampfer, K Faber

Index: Osprian, Ingrid; Stampfer, Wolfgang; Faber, Kurt Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 22 p. 3779 - 3785

Full Text: HTML

Citation Number: 14

Abstract

A series of (±)-2, 2-disubstituted oxiranes bearing an alkene or alkyne functional group were resolved by bacterial epoxide hydrolases with excellent selectivities. The presence of a carbon–carbon double or triple bond furnished a highly flexible system for substrate modification, which allowed the enantioselectivity to be tuned by rational substrate modification. Thus, a significant selectivity enhancement of more than a ten-fold increase ...