An Ugi-Type Condensation of α-Isocyanoacetamide and Chiral Cyclic Imine under a New Catalytic System

Sheng Li; Ruijiao Chen; Xiubing Liu; Li Pan; Liang Xia; Xiaochuan Chen

doi:10.1055/s-0032-1316549

Synlett, Table of Contents

Synlett 2012; 23(13): 1985-1989
DOI: 10.1055/s-0032-1316549

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An Ugi-Type Condensation of α-Isocyanoacetamide and Chiral Cyclic Imine under a New Catalytic System

Sheng Li

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China

,

Ruijiao Chen

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China

,

Xiubing Liu

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China

,

Li Pan

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China

,

Liang Xia

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China

,

Xiaochuan Chen*

^aKey Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, P. R. of China

^bState Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, P. R. of China, Fax: +86(28)85413712 Email: chenxc@scu.edu.cn

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Abstract

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Abstract

A new catalytic Ugi-type condensation of α-isocyanoacetamide and chiral cyclic imine is developed, where the combination of phenyl phosphilic acid and trifluoroethanol is exploited to promote the Ugi-type condensation with α-isocyanoacetamide for the first time. Under this new catalytic system, the reaction using the cyclic imines as relatively inertial substrates proceed well, and chiral 3-oxazolyl-morpholin/piperazine-2-one derivatives are synthesized with high yield and stereoselectivity. Furthermore, transformation of the condensation product to a novel fused tricyclic structure is attempted initially by treatment with maleic anhydride.

Key words

catalytic Ugi-type condensation - α-isocyanoacetamide - oxazoles - phosphilic acid - asymmetric synthesis

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References and Notes

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