Dynamic Kinetic Resolution of 1,3-Dihydro-2H-isoindole-1-carboxylic Acid Methyl Ester: Asymmetric Transformations toward Isoindoline Carbamates
journal contributionposted on 2012-04-06, 00:00 authored by Roberto Morán-Ramallal, Vicente Gotor-Fernández, Pedro Laborda, Francisco J. Sayago, Carlos Cativiela, Vicente Gotor
Asymmetric syntheses of isoindoline carbamates have been successfully achieved through enzyme-mediated dynamic kinetic resolution processes and without requirement of metal or acid–base catalyst for the substrate racemization. Optically active carbamates were obtained in good yields and an excellent degree of stereoselectivity when Pseudomonas cepacia lipase (PSL) was used as biocatalyst, with diallyl or dibenzyl carbonates being both adequate reagents in alkoxycarbonylation reactions.
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substrate racemizationrequirementstereoselectivitybiocatalystalkoxycarbonylation reactionsacidOpticallyAsymmetric TransformationsMethyl EsterPseudomonas cepacia lipaseIsoindoline CarbamatesAsymmetric synthesesdiallylresolution processesDynamic Kinetic Resolutionreagentcatalystisoindoline carbamatesDihydroPSLyielddibenzyl carbonates