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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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Publication details

The article was received on 17 Aug 2014, accepted on 22 Sep 2014 and first published on 23 Sep 2014


Article type: Communication
DOI: 10.1039/C4OB01759E
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 9324-9328
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    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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