Kinetic Resolutions and Enantioselective Transformations of 5-(Acyloxy)pyrrolinones Using Candida antarctica Lipase B:Synthetic and Structural Aspects

Various 5-(acyloxy)pyrrolinones have been prepared in enantiomerically pure form by means of an enzymatic resolution or an asymmetric transformation. Either enantiomer is obtained using the same enzyme, Candida antarctica lipase B, by modification of the procedure from transesterification to esterif...

Full description

Bibliographic Details
Published in:The Journal of Organic Chemistry
Main Authors: Cuiper, A.D, Kouwijzer, M.L C E, Grootenhuis, P.D J, Kellogg, R.M, Feringa, B.L.
Format: Article in Journal/Newspaper
Language:English
Published: 1999
Subjects:
CHIRAL BUILDING-BLOCKS
ENZYMATIC RESOLUTION
CATALYZED RESOLUTION
ALCOHOL ENANTIOMERS
EFFICIENT SYNTHESIS
COMPLEXES
ACID
RECOGNITION
INHIBITOR
SUBSTRATE
Antarc*
Antarctica
Online Access:https://hdl.handle.net/11370/1ec1fdb0-6048-4879-8fe8-a5c60c17c6a2
https://research.rug.nl/en/publications/1ec1fdb0-6048-4879-8fe8-a5c60c17c6a2
https://doi.org/10.1021/jo991062e
Description
Summary:Various 5-(acyloxy)pyrrolinones have been prepared in enantiomerically pure form by means of an enzymatic resolution or an asymmetric transformation. Either enantiomer is obtained using the same enzyme, Candida antarctica lipase B, by modification of the procedure from transesterification to esterification. N-Acyl-5-(acyloxy)pyrrolinones 1 (R2 = acyl) are synthesized by applying this method with 100% yield and >99% ee. To rationalize the observed enantioselectivity and the substituent effects of these reactions both empirical models and molecular modeling studies have been used, and a qualitative agreement was found between the results from these studies and the experimental results.

Similar Items