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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 17
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Original Articles

Efficient Protocol for Stereoselective Epoxidation of Cinnamic Esters Using TsNBr2

, &
Pages 2647-2652 | Received 02 May 2009, Published online: 05 Aug 2010
 

Abstract

An efficient method has been developed for the synthesis of epoxide from cinnamic esters without any catalyst. The reaction was performed in CH3CN–water (4:1) using N,N-dibromo-p-toluenesulfonamide (TsNBr2) in alkaline conditions. This procedure can be utilized for stereoselective synthesis of epoxides from cinnamic esters in excellent yield in a shorter reaction time with exclusive formation of the trans-isomer. The method was further extended successfully for styrenes.

ACKNOWLEDGMENT

Financial support from the Department of Science and Technology (Grant No. SR/S1/RFPC-07/2006) is gratefully acknowledged.

Notes

a Reaction conditions: ethyl cinnamate (1.1 mmol), MeCN (4 mL), H2O (1 mL), TsNBr2 (1.2 mmol), K2CO3 (1.5 mmol), room temperature.

b Isolated yield after chromatographic purifications.

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