Synergistic gold and enamine catalysis: intermolecular α-alkylation of aldehydes with allenamides

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URI: http://hdl.handle.net/10347/14565
ISSN: 1359-7345
DOI: 10.1039/C5CC09533F

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2016-01-08

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Royal Society of Chemistry
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Abstract

Aldehydes can be α-alkylated with allenamides by the combined action of an organocatalyst and a gold complex. The reaction requires the simultaneous generation of an enamine and a gold-activated allenamide. Importantly, by using a chiral amine as organocatalyst it is possible to obtain aldehyde products featuring all-carbon quaternary stereocenter at their α-position, with moderate to good levels of enantioselectivity

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NOTICE: This is the peer reviewed version of the following article: Jaime Fernández-Casado, Ronald Nelson, José L. Mascareñas* and Fernando López* (2016), Synergistic Gold and Enamine Catalysis: Intermolecular α-Alkylation of Aldehydes with Allenamides. ChemComm., 52, 2909-2912 [10.1039/C5CC09533F]. This article may be used for non-commercial purposes in accordance with RSC Terms and Conditions for self-archiving

Keywords

Aldehydes| Allenamides| Enantioselectivity| Gold complex| Organocatalyst

Bibliographic citation

Fernández-Casado, J., Nelson, R., Mascareñas, J.L. and López, F. (2016), Synergistic gold and enamine catalysis: intermolecular α-alkylation of aldehydes with allenamides. Chem. Commun., 52, 2909-2912 [DOI:10.1039/C5CC09533F]

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This work was supported by the Spanish MINECO (SAF2013-41943-R), the ERDF, the European Research Council (Adv. Grant No. 340055) and the Xunta de Galicia (GRC2013-041)

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Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
Química Orgánica