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Enantioselective Organocatalytic Alkylation of Aldehydes and Enals Driven by the Direct Photoexcitation of Enamines

Mattia Silvi, Elena Arceo, Igor D. Jurberg, Carlo Cassani and Paolo Melchiorre*

*ICIQ−Institute of Chemical Research of Catalonia, Av. Pa´sos Catalans 16, 43007 Tarragona, Spain, Email: pmelchiorreiciq.es

M. Silvi, E. Arceo, I. D. Jurberg, C. Cassani, P. Melchiorre, J. Am. Chem. Soc., 2015, 137, 6120-6123.

DOI: 10.1021/jacs.5b01662 (free Supporting Information)


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Abstract

A photo-organocatalytic enantioselective α- and γ-alkylation of aldehydes and enals with bromomalonates occurs under illumination by a fluorescent light bulb in the presence of a commercially available aminocatalyst without any external photoredox catalyst. Mechanistic investigations reveal the ability of transiently generated enamines to directly reach an electronically excited state while reactive radical species from the organic halides are formed.

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Key Words

carbonyl compounds, active methylene compounds, organocatalysis


ID: J48-Y2015