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Enantiopure N ‐Benzyloxycarbonyl‐β 2 ‐amino Acid Allyl Esters from Racemic β‐Lactams by Dynamic Kinetic Resolution using Candida antarctica Lipase B
Author(s) -
Gianolio Eleonora,
Mohan Resmi,
Berkessel Albrecht
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500820
Subject(s) - candida antarctica , enantiopure drug , kinetic resolution , chemistry , lipase , resolution (logic) , hydrolysis , organic chemistry , catalysis , stereochemistry , enzyme , enantioselective synthesis , artificial intelligence , computer science
Abstract The dynamic kinetic resolution of α‐substituted racemic β‐lactams by alcoholytic ring‐opening, catalyzed by immobilized lipase B from Candida antarctica is described. With this process, a variety of racemic α‐substituted N ‐Cbz‐azetidinones (Cbz=benzyloxycarbonyl) was transformed to the corresponding N ‐Cbz‐protected β 2 ‐amino acid allyl esters with high enantioselectivity (up to 99%) and high yields (up to quantitative) at room temperature.