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Synthesis 2009(7): 1123-1126
DOI: 10.1055/s-0028-1087999
DOI: 10.1055/s-0028-1087999
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
A Simple and Efficient Oxidation Procedure for the Synthesis of Acid-Sensitive Epoxides
Further Information
Received
20 October 2008
Publication Date:
06 March 2009 (online)
Publication History
Publication Date:
06 March 2009 (online)
Abstract
A mild and straightforward epoxidation protocol based on sodium perborate as primary oxidant and sodium dehydrocholate as organomediator under homogeneous conditions is described. In particular, geraniol, linalool, 3-carene, and α-pinene are quantitatively converted into the corresponding 6,7-epoxides and trans-epoxides, respectively. The bile acid salt is recovered from the reaction mixture and may be reused with unchanged efficiency and selectivity.
Key words
perborate - sodium dehydrocholate - epoxidation - organomediator - terpene oxidation
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