Facile Methods for the Separation of the cis- and trans-Diastereomers of Limonene­ 1,2-Oxide and Convenient Routes to Diequatorial and Diaxial 1,2-Diols

Abstract

Facile methods are described for accessing four dia­stereomerically pure products from the commercial mixture of limonene­ oxide. The use of either an aqueous mercury(II)-mediated or H⁺-catalysed hydration, afforded a kinetic separation of (+)-limonene­ oxide (cis- or trans-isomer could be respectively recovered) from the commercially available diastereomeric mixture in good recovery yields and high diastereoselectivity (>98% de). The hydrolysed limonene oxide products, either trans-diequatorial or trans-diaxial diols, are also formed in good conversion yields and high diastereoselectivity (>98% de).

Key words

kinetic separation - diastereomer resolution - limonene oxide - mercury - diols

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18

The X-ray crystal data of 4 (CCDC-627386) can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.