3 years ago

Direct Stereoselective Installation of Alkyl Fragments at the β-Carbon of Enals via Excited Iminium Ion Catalysis

Direct Stereoselective Installation of Alkyl Fragments
at the β-Carbon of Enals via Excited Iminium Ion Catalysis
Mattia Silvi, Hamish B. Hepburn, Nurtalya Alandini, Charlie Verrier, Cristofer Pezzetta, Alberto Vega-Peñaloza, Mauro Moliterno, Luca Buzzetti, Paolo Melchiorre
The direct introduction of sp3 carbon fragments at the β position of α,β-unsaturated aldehydes is greatly complicated by competing 1,2-addition manifolds. Previous catalytic enantioselective conjugate addition methods, based on the use of organometallic reagents or ground-state iminium ion activation, could not provide general and efficient solutions. We report herein that, by turning them into strong oxidants, visible light excitation of chiral iminium ions triggers a stereocontrolled radical pathway that exclusively affords highly enantioenriched β-substituted aldehydes bearing a variety of alkyl fragments.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b03788

DOI: 10.1021/acscatal.7b03788

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