Distinct reactivity of Morita–Baylis–Hillman acetates as a novel C2 component in amine-catalyzed [2 + 2 + 2] and [2 + 4] annulations

Rongshun Chen; Silong Xu; Liyi Wang; Yuhai Tang; Zhengjie He

doi:10.1039/C3CC41419A

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Chemical Communications

Issue 34, 2013

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Distinct reactivity of Morita–Baylis–Hillman acetates as a novel C₂ component in amine-catalyzed [2 + 2 + 2] and [2 + 4] annulations

Rongshun Chen,^a Silong Xu,*^b Liyi Wang,^a Yuhai Tang^b and Zhengjie He*^a

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The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, Tianjin 300071, P.R. China
E-mail: zhengjiehe@nankai.edu.cn

Department of Chemistry, School of Science, Xi'an Jiaotong University, Xi'an 710049, P.R. China
E-mail: silongxu@mail.xjtu.edu.cn

Chem. Commun., 2013,49, 3543-3545

DOI: 10.1039/C3CC41419A
Received 24 Feb 2013, Accepted 13 Mar 2013
First published online 14 Mar 2013

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Amine-catalyzed [2 + 2 + 2] and [2 + 4] annulations of Morita–Baylis–Hillman (MBH) acetates with cyano activated alkenes and 1,3-azadienes have been developed to provide cyclohexanes and tetrahydropyridines. In the annulations, MBH acetates serve as a novel C₂ component with an inactive homoallylic methyl involved in the bond formation.

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Silong Xu
Liyi Wang
Yuhai Tang
Zhengjie He

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Chemical Communications

Distinct reactivity of Morita–Baylis–Hillman acetates as a novel C₂ component in amine-catalyzed [2 + 2 + 2] and [2 + 4] annulations

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Distinct reactivity of Morita–Baylis–Hillman acetates as a novel C2 component in amine-catalyzed [2 + 2 + 2] and [2 + 4] annulations

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Distinct reactivity of Morita–Baylis–Hillman acetates as a novel C₂ component in amine-catalyzed [2 + 2 + 2] and [2 + 4] annulations