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Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine |
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| Authors: | Ferenc Faigl Ervin Kovács Dóra Balogh Tamás Holczbauer Mátyás Czugler Béla Simándi |
| Institution: | 1. Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Hungary 2. Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, H-1111, Budapest, Hungary 3. Institute of Structural Chemistry, Hungarian Academy of Sciences, H-1025, Budapest, Hungary 4. Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, H-1111, Budapest, Hungary |
| Abstract: | The first enzyme-catalyzed kinetic resolution of tert-butyl-3-hydroxy-4-phenylpyrrolidine-1-carboxylate is presented. Enzyme, solvent and temperature optimization resulted in a new resolution method with E = 40 enantioselectivity. The acetate derivative of the (+)-(3S,4R) enantiomer formed while the (?)-(3R,4S) isomer remained intact. Very good enantioselectivities (E > 200) were achieved in the enzyme-catalyzed alcoholysis of the racemic acetate in i-propanol and t-butanol where the (+)-(3S,4R) enantiomer was prepared in pure form (ee > 99.7%). Absolute configuration of the (?)-(3R,4S)-enantiomer was determined by single crystal X-ray diffraction method. |
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