| Abstract
| - An efficient lipase-catalyzed desymmetrization of prochiral 2,2-disubstituted 1,3-propanediols wasdeveloped using 1-ethoxyvinyl 2-furoate 1b, for which the well-known method using vinyl orisopropenyl acetate has had limited success due to low reactivity and easy racemization of theproducts through acyl group migration. The reagent 1b is highly reactive and converts variousprochiral 1,3-diols to the monoesters having a chiral quaternary carbon center with 82−99% ee.These products were stable against racemization under acidic conditions, and their furoyl groupswere compatible with oxidative conditions. Prolonging the reaction time led to the kinetic resolutionof the monoesters resulting in an increase of their optical purity. The similar desymmetrization ofmeso cis-1,2-cycloalkanediols gave the monoesters with 82−97% ee without racemization.
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