Enzyme-catalyzed kinetic resolution of N-Boc-trans-3-hydroxy-4-phenylpyrrolidine

• Authors: Ferenc Faigl , Ervin Kovács , Dóra Balogh , Tamás Holczbauer , Mátyás Czugler , Béla Simándi
• Languages of publication: EN

Abstracts

EN

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. [...]

Keywords

EN

Enzyme-catalyzed resolution; Lipase enzymes; 3-hydroxy-4-phenylpyrrolidine; Enzymatic hydrolysis; Enantioselective alcoholysis

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2014
• Volume: 12
• Issue: 1
• Pages: 25-32

Dates

published

1 - 1 - 2014

online

27 - 10 - 2013

Contributors

author

Ferenc Faigl

author

Ervin Kovács

• Research Group for Organic Chemical Technology, Hungarian Academy of Sciences, H-1111, Budapest, Hungary

author

Dóra Balogh

• Department of Organic Chemistry and Technology, Budapest University of Technology and Economics, H-1111, Budapest, Hungary

author

Tamás Holczbauer

• Institute of Structural Chemistry, Hungarian Academy of Sciences, H-1025, Budapest, Hungary

author

Mátyás Czugler

• Institute of Structural Chemistry, Hungarian Academy of Sciences, H-1025, Budapest, Hungary

author

Béla Simándi

• Department of Chemical and Environmental Process Engineering, Budapest University of Technology and Economics, H-1111, Budapest, Hungary

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Identifiers

DOI

10.2478/s11532-013-0347-8