Organic & Biomolecular Chemistry 2009-12-07

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.

Zhenqiu Guo, Taoda Shi, Jun Jiang, Liping Yang, Wenhao Hu

Index: Org. Biomol. Chem. 7(23) , 5028-33, (2009)

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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.