Enantiopure N-Benzyloxycarbonyl-beta(2)-amino Acid Allyl Esters from Racemic beta-Lactams by Dynamic Kinetic Resolution using Candida antarctica Lipase B

The dynamic kinetic resolution of alpha-substituted racemic beta-lactams by alcoholytic ring-opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic a-substituted N-Cbz-azetidinones (Cbz = benzyloxycarbonyl) was transformed to the corr...

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Bibliographic Details
Main Authors: Gianolio, Eleonora, Mohan, Resmi, Berkessel, Albrecht
Format: Article in Journal/Newspaper
Language:English
Published: WILEY-V C H VERLAG GMBH 2016
Subjects:
ddc:no
Antarc*
Antarctica
Online Access:https://kups.ub.uni-koeln.de/28756/
Description
Summary:The dynamic kinetic resolution of alpha-substituted racemic beta-lactams by alcoholytic ring-opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic a-substituted N-Cbz-azetidinones (Cbz = benzyloxycarbonyl) was transformed to the corresponding N-Cbz-protected beta(2)-amino acid allyl esters with high enantioselectivity (up to 99%) and high yields (up to quantitative) at room temperature.

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