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| PAPER | Synthesis 2003: 2552-2558
DOI: 10.1055/s-2003-42416 |
© Georg Thieme Verlag Stuttgart · New York
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An Efficient Method for the Chemoselective Preparation of Benzoylated 1,2-Diols from Epoxides
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| A. Khalafi-Nezhad*, M. N. Soltani Rad, A. Khoshnood |
Department of Chemistry, College of Science, Shiraz University, Shiraz 71454, Iran
Fax: +98(711)2280926; e-Mail: khalafi@chem.susc.ac.ir;
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Received
28 June 2003 |
Abstract
A very efficient and highly regioselective ring-opening reaction of epoxides with benzoic acid and its derivatives in the presence of cat. amount of tetrabutylammonium bromide (TBAB) in anhydrous acetonitrile has been developed. This effective method is useful for the preparation of selectively protected diols as precursor for many organic syntheses such as those of acyclic nucleosides and other synthetic purposes. The advantages of this method are efficiency, selectivity, low cost, and the applicability in large-scale synthesis of b-benzoyloxyalkanols. Key words
benzoylated 1,2-diol - benzoic acid - epoxides - acetonitrile - TBAB
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