(S)-Selective Dynamic Kinetic Resolution of Secondary Alcohols by the Combination of Subtilisin and an Aminocyclopentadienylruthenium Complex as the Catalysts

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• 作者：Mahn-Joo Kim ; Yong Il Chung ; Yoon Kyung Choi ; Han Ki Lee ; Daeho Kim ; and Jaiwook Park
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：September 24, 2003
• 年：2003
• 卷：125
• 期：38
• 页码：11494 - 11495
• 全文大小：46K
• 年卷期：v.125,no.38(September 24, 2003)
• ISSN：1520-5126

文摘

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%).