Download PDF
Synthesis 2009(7): 1123-1126  
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

Olga Bortolini*a, Giancarlo Fantinb, Marco Fogagnolo*b
a Department of Chemistry, University of Calabria, Via Bucci 12 C, 87036 Rende (CS), Italy
Fax: +39(984)493307; e-Mail: o.bortolini@unical.it;
b Department of Chemistry, University of Ferrara, Via Borsari 46, 44100 Ferrara, Italy
e-Mail: fgr@unife.it;
Further Information

Publication History

Received 20 October 2008
Publication Date:
06 March 2009 (online)

   Buy Article Permissions and Reprints All articles of this category
Zoom Image

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