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Issue 46, 2014
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Trienamines derived from 5-substituted furfurals: remote ε-functionalization of 2,4-dienals

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Abstract

The selective ε-functionalization of 5-substituted furfurals via trienamine intermediates is reported herein. This methodology was successfully applied to several 5-substituted furfurals with different amines via formation of a trienamine through the furan ring. The rationalized reaction mechanism involves the addition of the trienamine intermediate to its corresponding iminium-ion producing new furan-containing scaffolds.

Graphical abstract: Trienamines derived from 5-substituted furfurals: remote ε-functionalization of 2,4-dienals

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Article information


Submitted
17 Aug 2014
Accepted
22 Sep 2014
First published
23 Sep 2014

Org. Biomol. Chem., 2014,12, 9324-9328
Article type
Communication
Author version available

Trienamines derived from 5-substituted furfurals: remote ε-functionalization of 2,4-dienals

J. A. S. Coelho, A. F. Trindade, V. André, M. Teresa Duarte, L. F. Veiros and C. A. M. Afonso, Org. Biomol. Chem., 2014, 12, 9324
DOI: 10.1039/C4OB01759E

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