Copper-Catalyzed Three-Component Tandem Reactions for the Synthesis of β-Carboalkoxy-γ-lactams

Zhengning Li; Yunyun Feng; Zengchang Li; Lan Jiang

doi:10.1055/s-0034-1379482

Synlett, Table of Contents

Synlett 2014; 25(20): 2899-2902
DOI: 10.1055/s-0034-1379482

letter

Copper-Catalyzed Three-Component Tandem Reactions for the Synthesis of β-Carboalkoxy-γ-lactams

Authors

Zhengning Li*

College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 Email: znli@dl.cn
Yunyun Feng

College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 Email: znli@dl.cn
Zengchang Li

College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 Email: znli@dl.cn
Lan Jiang

College of Environmental and Chemical Engineering, Dalian University, Dalian 116622, P. R. of China Fax: +86(411)87402449 Email: znli@dl.cn

Abstract

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Abstract

β-Carboalkoxy-γ-lactams were synthesized in high yields via copper-catalyzed three-component reactions of α,β-unsaturated dicarboxylate esters, aldimines, and a silane. The reaction proceeds in a tandem manner via conjugate reduction, Mannich reaction, and a subsequent lactamization. The method is attractive with regard to the flexible combination of easily available reactants, the mild conditions, and the high yields. It provides a concise synthetic route to functionalized lactams with a β-ester group.

Key words

tandem reaction - copper - catalysis - conjugate reduction - aldol addition - lactamization

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References

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