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Issue 53, 2015
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C–H functionalization of cyclic amines: redox-annulations with α,β-unsaturated carbonyl compounds

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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.

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

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Article information


Submitted
23 Apr 2015
Accepted
20 May 2015
First published
20 May 2015

Chem. Commun., 2015,51, 10648-10651
Article type
Communication
Author version available

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

Y. Kang, M. T. Richers, C. H. Sawicki and D. Seidel, Chem. Commun., 2015, 51, 10648
DOI: 10.1039/C5CC03390J

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