Synthesis of Spirocyclic Ethers by Enantioselective Copper‐Catalyzed Carboetherification of Alkenols

Spirocyclic ethers can be found in bioactive compounds. This copper‐catalyzed enantioselective alkene carboetherification provides 5,5‐, 5,6‐ and 6,6‐spirocyclic products containing fully substituted chiral carbon centers with up to 99 % enantiomeric excess. This reaction features the formation of t...

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Bibliographic Details
Published in:Angewandte Chemie 2018-09, Vol.130 (39), p.13103-13106
Main Authors: Karyakarte, Shuklendu D., Um, Chanchamnan, Berhane, Ilyas A., Chemler, Sherry R.
Format: Article
Language:English
Subjects:
Alkenes
Alkynes
Aromatic compounds
Bioactive compounds
Chemical synthesis
Chemistry
Copper
Copper compounds
Cyclisierungen
Enantiomers
Enantioselektivität
Ethers
Kupfer
Spiroverbindungen
Substrates
Synthesemethoden
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Summary:Spirocyclic ethers can be found in bioactive compounds. This copper‐catalyzed enantioselective alkene carboetherification provides 5,5‐, 5,6‐ and 6,6‐spirocyclic products containing fully substituted chiral carbon centers with up to 99 % enantiomeric excess. This reaction features the formation of two rings from acyclic substrates, 1,1‐disubstituted alkenols functionalized with either arenes, alkenes, or alkynes, and clearly constitutes a powerful way to synthesize chiral spirocyclic ethers. Doppelringe: Eine kupferkatalysierte enantioselektive Carboveretherung von Alkenen ergibt 5,5‐, 5,6‐ und 6,6‐Spirocyclen mit komplett substituierten Kohlenstoff‐Chiralitätszentren und Enantiomerenüberschüssen bis 99 %. Ausgehend von acyclischen 1,1‐disubstituierten Alkenolen mit Aren‐, Alken‐ oder Alkinfunktion ebnet diese Reaktion den Weg für die Synthese chiraler spirocyclischer Ether durch Bildung von zwei Ringen.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201808554