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2004
Oxirane derivatives
R 0030
Efficient Synthesis of α,β-Epoxy Carbonyl Compounds in Acetonitrile: Darzens
of Aromatic Aldehydes with Ethyl Chloroacetate. — The Darzens
51- 085 Condensation
reaction of ethyl chloroacetate (II) and aromatic aldehydes proceeds in the presence of
phase-transfer catalysts like polymer-supported cinchonidium chloride or tetrahexylammonium bromide under mild conditions with high yields and with a fair degree of
stereoinduction. It is found that the diastereoselectivity of the reaction can be reversed
by the choice of MeCN instead of THF as solvent. — (WANG, Z.-T.; XU*, L.-W.;
XIA, C.-G.; WANG, H.-Q.; Helv. Chim. Acta 87 (2004) 8, 1958-1962; State Key Lab.
Oxo Synth. Sel. Oxid., Lanzhou Inst. Chem. Phys., Chin. Acad. Sci., Lanzhou 730000,
Gansu, Peop. Rep. China; Eng.) — Bartels
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