Evaluation of enantioselectivity in lipase-catalyzed acylation of hydroxyalkylphosphine oxides

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• 作者：Kosei Shioji ; Takafumi Ueyama ; Nobuaki Ueda ; Emiko Mutoh ; Tsutomu Kurisaki ; Hisanobu Wakita ; Kentaro Okuma
• 关键词：Lipase ; Optical resolution ; Hydroxyalkylphosphine oxides
• 刊名：Journal of Molecular Catalysis B: Enzymatic
• 出版年：2008
• 出版时间：November 2008
• 年：2008
• 卷：55
• 期：3-4
• 页码：146-151
• 全文大小：440 K

文摘

The lipase-catalyzed optical resolution of 2-, 3-, and 5-hydroxyalkyl phosphorus compounds 1 provided the corresponding optically pure diastereomers in good yields. (S_P, R)- and (R_P, S)-1 were acylated faster than (S_P, S)- and (R_P, R)-1. The stereoselectivity at the phosphorus atom changed with the flexibility of the active sites in the lipases. The stereoselectivity at the phosphorus atom was higher in the reaction of 1a than in the reaction of 1b,c. The reaction rate of -hydroxyalkylphosphine oxide 1c was faster than that of 1a, although less enantioselectivity was observed at the phosphorus atom.