Catalytic Asymmetric Oxidative [gamma]-Coupling of [alpha],[beta]-Unsaturated Aldehydes with Air as the Terminal Oxidant

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 [...

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Veröffentlicht in:	Angewandte Chemie 2018-02, Vol.130 (6), p.1622
Hauptverfasser:	Naesborg, Line, Corti, Vasco, Leth, Lars Astrup, Poulsen, Pernille H, Jorgensen, Karl Anker
Format:	Artikel
Sprache:	ger
Schlagworte:	Aldehydes Catalysis Chemical reactions Chemistry Copper compounds Coupling Oxidation Salts
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creator	Naesborg, Line Corti, Vasco Leth, Lars Astrup Poulsen, Pernille H Jorgensen, Karl Anker
description	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 [alpha],[beta]-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 [gamma]-homo- and [gamma]-heterocoupling reactions. In the majority of examples presented, only a single stereoisomer was formed.
doi_str_mv	10.1002/ange.201711944
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subjects	Aldehydes Catalysis Chemical reactions Chemistry Copper compounds Coupling Oxidation Salts
title	Catalytic Asymmetric Oxidative [gamma]-Coupling of [alpha],[beta]-Unsaturated Aldehydes with Air as the Terminal Oxidant
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