Lipase-catalyzed resolution of β-hydroxy selenides |
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| Affiliation: | 1. Graduate School of Life Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan;2. Department of Materials Chemistry, Faculty of Science and Technology, Ryukoku University, Otsu, Shiga 520-2194, Japan;1. Chemistry Department, Faculty of Science, Fayoum University, Fayoum, Egypt;2. Central European Institute of Technology (CEITEC), Brno University of Technology, Purkyňova 464/118, 612 00 Brno, Czech Republic;3. Brno University of Technology, Faculty of Chemistry, Institute of Physical and Applied Chemistry, Purkyňova 464/118, 612 00 Brno, Czech Republic;4. Petrochemical Research Chair, Chemistry Department, College of Science, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia;5. Chemistry Department, Faculty of Science, Ain Shams University, Cairo, Egypt;6. Textile Research Division, National Research Center, Dokki, PO Box 12622, Giza 12522, Egypt |
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| Abstract: | Eleven β-hydroxy selenides were kinetically resolved using an immobilized lipase (Amano PS-C II) in toluene in the presence of vinyl acetate at 30 °C. This approach provided, in several cases, both enantiomers in high enantiomeric excess. The role of the size of substituents and the behaviour of cyclic β-hydroxy selenides is also discussed. Enantiopure β-hydroxy selenides are useful building blocks. As an application of this chemistry, enantiopure (1S,2R)-indene oxide was obtained in one step from the proper enantiopure β-hydroxy selenide. |
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