Catalytic Asymmetric Oxidative γ‐Coupling of α,β‐Unsaturated Aldehydes with Air as the Terminal Oxidant |
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Authors: | Line Næsborg Vasco Corti Lars Astrup Leth Dr. Pernille H. Poulsen Prof. Karl Anker Jørgensen |
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Affiliation: | Department of Chemistry, Aarhus University, Aarhus, Denmark |
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Abstract: | A novel concept for catalytic asymmetric coupling reactions is presented. Merging organocatalysis with single‐electron oxidation by using a catalytic amount of a copper(II) salt and air as the terminal oxidant, we have developed a highly stereoselective carbon–carbon oxidative coupling reaction of α,β‐unsaturated aldehydes. The concept relies on the generation of a dienamine intermediate, which is oxidized to an open‐shell activated species that undergoes highly selective γ‐homo‐ and γ‐heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed. |
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Keywords: | asymmetric catalysis organocatalysis oxidative coupling single-electron transfer synthetic methods |
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