Evaluation of enantioselectivity in lipase-catalyzed acylation of hydroxyalkylphosphine oxides |
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| Institution: | 1. Department of Chemistry and Pharmaceutical Sciences, Vrije Universiteit Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands;2. Department of Chemistry, University of Johannesburg, Auckland Park, Johannesburg 2006 South Africa;1. Pharmacy School, Jiangsu University, Xuefu Road 301, Zhenjiang City, Jiangsu, 212013, China;2. Jiangsu University Library, Xuefu Road 301, Jiangsu, 212013, China;3. Department of Chemistry, Mississippi State University, 39762 MS State, USA;1. Department of Chemistry, Visva-Bharati (A Central University), Santiniketan, 731235, India;2. Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, 620002, Yekaterinburg, Russian Federation;3. I. Ya. Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620219, Yekaterinburg, Russian Federation |
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| Abstract: | The lipase-catalyzed optical resolution of 2-, 3-, and 5-hydroxyalkyl phosphorus compounds 1 provided the corresponding optically pure diastereomers in good yields. (SP, R)- and (RP, S)-1 were acylated faster than (SP, S)- and (RP, 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. |
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