Journal
SYNLETT
Volume -, Issue 5, Pages 842-844Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-2005-864799
Keywords
Darzens reaction; ammonium ylides; 2,3-diaryl epoxides
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The Darzens reaction using electron deficient p-substituted benzyltriethylammonium chlorides with aromatic aldehydes afforded 2,3-diaryl epoxides with trans selectivity (> 99%) while the corresponding reaction with electron releasing p-substituted benzyltriethylammonium salts gave the epoxides as diastereomeric mixtures. Epoxide formation of p-trifluoromethylbenzylammonium salt, prepared from p-trifluoromethylbenzyl chloride and DABCO, afforded the corresponding 2,3-diaryl epoxide in high yield (> 98%).
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