Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 6, Pages 1606-1610Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201711944
Keywords
asymmetric catalysis; organocatalysis; oxidative coupling; single-electron transfer; synthetic methods
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Funding
- Carlsberg Foundation Semper Ardens programme
- FNU
- Aarhus University
- DNRF
- Alma Mater Studiorum-University of Bologna
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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.
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