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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 5
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Original Articles

One-Pot Catalytic Conversion of Epoxides to 1,2-Diacetates with Hydride Transferring Agents in Acetic Anhydride

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Pages 637-644 | Received 13 Nov 2009, Published online: 31 Jan 2011
 

Abstract

Direct transformation of structurally different epoxides to the corresponding 1,2-diacetates was studied with catalytic amounts of NaBH4, LiAlH4, CaH2, and NaH. The reactions were carried out in refluxing acetic anhydride within 1.5–2.5 h to give vic-diacetates in good to excellent yields. Conversion of R-(+)-styrene oxide to S-(+)-1,2-diacetoxy-1-phenylethane was carried out with good yield and stereospecificity with the NaBH4/Ac2O system at 0 °C.

ACKNOWLEDGMENT

We acknowledge the financial support of this work by the Research Council of Urmia University.

Notes

a All reactions were carried out in the presence of NaBH4 (0.2 eq) in refluxing Ac2O (1 mL).

b Yields refer to isolated pure products.

a All reactions were carried out with 0.2 eq hydride reagents in refluxing Ac2O (1 mL).

b Yields refer to isolated pure products.

a Amount of catalyst per 1 mmol of epoxide.

b Reaction time was not reported, however, 24 h was the reported time for ring openning–acetolysis of N-tosylaziridines.

c No reaction occured on aromatic epoxides.

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