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- Title
Catalytic Asymmetric Oxidative γ‐Coupling of α,β‐Unsaturated Aldehydes with Air as the Terminal Oxidant.
- Authors
Næsborg, Line; Corti, Vasco; Leth, Lars Astrup; Poulsen, Pernille H.; Jørgensen, Karl Anker
- Abstract
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.
- Subjects
COUPLING reactions (Chemistry); ALDEHYDE reactivity; ORGANOCATALYSIS; CARBON-carbon bonds; OXIDATIVE coupling kinetics
- Publication
Angewandte Chemie, 2018, Vol 130, Issue 6, p1622
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201711944