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Organic & biomolecular chemistry

Component match in rhodium catalyzed three-component reactions of ethyl diazoacetate, H2O and aryl imines: a highly diastereoselective one-step synthesis of beta-aryl isoserine derivatives.


PMID 19907795

Abstract

Water and ethyl diazoacetate were found to be matched components for generating highly reactive nucleophilic oxonium ylide in the presence of a dirhodium acetate catalyst. Simultaneous trapping of the oxonium ylide intermediate with aryl imines gave beta-aryl isoserine derivatives with high diastereoselectivity.