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. 2015 Jul 7;51(53):10648-51.
doi: 10.1039/c5cc03390j.

C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds

YoungKu Kang  1 , Matthew T Richers, Conrad H Sawicki, Daniel Seidel
Affiliations

C-H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds

YoungKu Kang et al. Chem Commun (Camb). .

Abstract

Cyclic amines such as pyrrolidine and 1,2,3,4-tetrahydroisoquinoline undergo redox-annulations with α,β-unsaturated aldehydes and ketones. Carboxylic acid promoted generation of a conjugated azomethine ylide is followed by 6π-electrocylization, and, in some cases, tautomerization. The resulting ring-fused pyrrolines are readily oxidized to the corresponding pyrroles or reduced to pyrrolidines.

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Figures

Scheme 1
Scheme 1
Scope of the reaction with pyrrolidine.
Scheme 2
Scheme 2
Scope of the reaction with cinnamaldehydes.
Scheme 3
Scheme 3
Product transformation.
See this image and copyright information in PMC

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