Synthesis 2007(10): 1523-1527  
DOI: 10.1055/s-2007-966033
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Michael Blair, Philip C. Andrews, Benjamin H. Fraser, Craig M. Forsyth, Peter C. Junk, Massimiliano Massi, Kellie L. Tuck*
School of Chemistry, Monash University, Clayton, Victoria, Australia 3800
Fax: +61(3)99054597; e-Mail: kellie.tuck@sci.monash.edu.au;
Further Information

Publication History

Received 9 January 2007
Publication Date:
02 May 2007 (online)

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).

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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.