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Efficient Synthesis of α,β-Epoxy Carbonyl Compounds in Acetonitrile: Darzens Condensation of Aromatic Aldehydes with Ethyl Chloroacetate

✍ Scribed by Zong-Ting Wang; Li-Wen Xu; Chun-Gu Xia; Han-Qing Wang


Publisher
John Wiley and Sons
Year
2004
Tongue
German
Weight
86 KB
Volume
87
Category
Article
ISSN
0018-019X

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✦ Synopsis


Abstract

The Darzens reaction of ethyl 2‐chloroacetate (1) with aromatic aldehydes 2 in the presence of polymer‐supported or nonsupported quaternary ammonium salts proceeds under mild conditions by phase‐transfer catalysis to give the corresponding epoxides 3 in satisfactory yields (Tables 1 and 2). With both MeCN as solvent and polystyrene‐supported catalysts, diastereoselective Darzens reactions proceed in excellent yields and short times, with a fair degree of stereoinduction.


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