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...

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Published inJournal of organic chemistry Vol. 64; no. 26; pp. 9529 - 9537
Main Authors Cuiper, Agnes D, Kouwijzer, Milou L. C. E, Grootenhuis, Peter D. J, Kellogg, Richard M, Feringa, Ben L
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 24.12.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENZYMATIC RESOLUTION
CHIRAL BUILDING-BLOCKS
ACID
RECOGNITION
CATALYZED RESOLUTION
SUBSTRATE
COMPLEXES
EFFICIENT SYNTHESIS
ALCOHOL ENANTIOMERS
INHIBITOR
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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.
Bibliography:istex:49C4E38C028F48C570471380154FE45410CAD423
ark:/67375/TPS-K0B75SKM-L
ISSN:0022-3263
1520-6904
DOI:10.1021/jo991062e