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Efficient Synthesis of α , β ‐Epoxy Carbonyl Compounds in Acetonitrile: Darzens Condensation of Aromatic Aldehydes with Ethyl Chloroacetate
Author(s) -
Wang ZongTing,
Xu LiWen,
Xia ChunGu,
Wang HanQing
Publication year - 2004
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200490177
Subject(s) - chemistry , acetonitrile , catalysis , organic chemistry , solvent , condensation , epoxy , thermodynamics , physics
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.