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Iron-catalyzed cascade cyanoalkylation/radical dearomatization of N-phenylcinnamamides: access to cyanoalkylated 1-azaspiro[4.5]decanes

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Abstract

An iron-catalyzed cascade radical cyanoalkylative dearomatization of N-phenyl cinnamamides was developed. A direct access to the 1-azaspiro[4.5]decanes motif with good regioselectivity and diastereoselectivity was provided, which was initiated by cyanoalkylation of alkenes. Functionalization of the C(sp3)–H bond and construction of two C(sp3)–C(sp3) bonds were involved in one step.

Graphical abstract: Iron-catalyzed cascade cyanoalkylation/radical dearomatization of N-phenylcinnamamides: access to cyanoalkylated 1-azaspiro[4.5]decanes

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Publication details

The article was received on 27 Feb 2017, accepted on 23 Mar 2017 and first published on 24 Mar 2017


Article type: Research Article
DOI: 10.1039/C7QO00157F
Citation: Org. Chem. Front., 2017, Advance Article
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    Iron-catalyzed cascade cyanoalkylation/radical dearomatization of N-phenylcinnamamides: access to cyanoalkylated 1-azaspiro[4.5]decanes

    H. Zhang and C. Zhu, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00157F

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