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Karl Anker Jørgensen

Catalytic Asymmetric Oxidative γ-Coupling of α,β-Unsaturated Aldehydes with Air as the Terminal Oxidant

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DOI

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.

Original languageEnglish
JournalAngewandte Chemie - International Edition
Volume57
Issue6
Pages (from-to)1606-1610
Number of pages5
ISSN1433-7851
DOIs
Publication statusPublished - 5 Feb 2018

    Research areas

  • asymmetric catalysis, organocatalysis, oxidative coupling, single-electron transfer, synthetic methods

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