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

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

doi:10.1039/B915013G

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

Zhenqiu Guo,^a Taoda Shi,^a Jun Jiang,^a Liping Yang^a and Wenhao Hu*^a

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* Corresponding authors

^a Department of Chemistry, East China Normal University, Shanghai 200062, P. R. China
E-mail: whu@chem.ecnu.edu.cn
Fax: +86-021-62233176

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 β-aryl isoserine derivatives with high diastereoselectivity.

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Article information

DOI: https://doi.org/10.1039/B915013G
Article type: Paper
Submitted: 24 Jul 2009
Accepted: 09 Sep 2009
First published: 12 Oct 2009

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Org. Biomol. Chem., 2009,7, 5028-5033

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

Z. Guo, T. Shi, J. Jiang, L. Yang and W. Hu, Org. Biomol. Chem., 2009, 7, 5028 DOI: 10.1039/B915013G

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Organic & Biomolecular Chemistry