A simple kinetic separation of (1:1) diastereomeric mixture of limonene oxides was used to purify
cis-and trans-diastereomers of (R)-(+)-limonene oxide. The epoxide ring of trans-isomer was selectively
opened by (R)-N-methyl-(α-methyl-benzyl)amine. This secondary nucleophilic amine left cis-limonene
oxide largely unreacted and was obtained up to 90% yield. In a diverse way, (R)-N-(α-methylbenzyl)
ethyl carbamate, selectively catalyze hydrolysis of cis-limonene oxide to 1,2-limonene diol
leaving trans-limonene oxide largely unreacted. The unreacted trans-limonene oxide was recovered
in up to 75% yield. HPLC and NMR analyses were used to demonstrate that the isolation of cis-and
trans-diastereomers of (R)-(+)-limonene oxide has shown that > 98% were pure. As a result, depending
on the realization of the secondary amine or carbamate in the presence of water, either cis-or
trans-limonene oxide may be obtained in high diastereomeric purity.
Faculty Opinions recommendation of Kinetic Separation of Oxidative and Non-oxidative Metabolism in Single Phagosomes from Alveolar Macrophages: Impact on Bacterial Killing.
