Open AccessKinetic Separation of cis-and trans-Limonene Epoxide: Reaction of Diastereomeric Mixture of Limonene Oxides with Secondary Amine and Carbamate
Author(s) -
Mohamed Merouane El Hammoumi,
Lyazid Ait Said,
A. El Bachiri,
Mostafa Khoukhi
Publication year - 2021
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2021.23379
Subject(s) - chemistry , diastereomer , limonene , epoxide , organic chemistry , amine gas treating , cis–trans isomerism , yield (engineering) , substituent , chromatography , catalysis , materials science , essential oil , metallurgy
A simple kinetic separation of (1:1) diastereomeric mixture of limonene oxides was used to purifycis-and trans-diastereomers of (R)-(+)-limonene oxide. The epoxide ring of trans-isomer was selectivelyopened by (R)-N-methyl-(α-methyl-benzyl)amine. This secondary nucleophilic amine left cis-limoneneoxide 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 diolleaving trans-limonene oxide largely unreacted. The unreacted trans-limonene oxide was recoveredin up to 75% yield. HPLC and NMR analyses were used to demonstrate that the isolation of cis-andtrans-diastereomers of (R)-(+)-limonene oxide has shown that > 98% were pure. As a result, dependingon the realization of the secondary amine or carbamate in the presence of water, either cis-ortrans-limonene oxide may be obtained in high diastereomeric purity.