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Catalytic Asymmetric Oxidative γ‐Coupling of α,β‐Unsaturated Aldehydes with Air as the Terminal Oxidant
Author(s) -
Næsborg Line,
Corti Vasco,
Leth Lars Astrup,
Poulsen Pernille H.,
Jørgensen Karl Anker
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201711944
Subject(s) - chemistry , catalysis , stereoselectivity , oxidative coupling of methane , organocatalysis , enantioselective synthesis , oxidative phosphorylation , copper , radical , coupling (piping) , photochemistry , combinatorial chemistry , organic chemistry , materials science , biochemistry , metallurgy
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.