AI Article Synopsis
- A new method for dynamic kinetic resolution (DKR) of racemic alcohols is introduced, utilizing surfactant-treated subtilisin for (S)-selective resolution and a ruthenium complex for racemization.
- The optimal DKR conditions involve using trifluoroethyl butyrate in THF at room temperature, resulting in high optical purity and good yields for eight different secondary alcohols.
- This subtilisin-based DKR shows complementary stereoselectivity to lipase-based DKR, achieving greater than 99.5% enantiomeric excess with high yields for acyl-carrying alcohols.
Article Abstract
A new procedure for the dynamic kinetic resolution (DKR) of racemic alcohols into single enantiomers is described. This procedure employs surfactant-treated subtilisin as an (S)-selective resolving catalyst and an aminocyclopentadienylruthenium complex as a racemizing catalyst. The DKR is performed best in the presence of an acyl donor such as trifluoroethyl butyrate in THF at room temperature. Eight simple secondary alcohols have been efficiently resolved with high optical purities and good yields. The subtilisin-based DKR is complementary in stereoselectivity to its lipase-based counterpart. For an acyl-carrying alcohol, both subtilisin- and lipase-based DKRs have proceeded equally well to give a pair of enantiomeric products (>99.5% ee each) with opposite optical rotations in high yields (94-95%).
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| http://dx.doi.org/10.1021/ja036766r | DOI Listing |
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