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

Wang ZongTing | Zendy; Xu LiWen | Zendy; Xia ChunGu | Zendy; Wang HanQing | Zendy

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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

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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