A Silver‐Catalyzed Modular Intermolecular Access to 6,6‐Spiroketals

A Silver‐Catalyzed Modular Intermolecular Access to 6,6‐Spiroketals

A modular synthesis of 6,6‐spiroketals via silver catalysis is reported. By combining an intermolecular Michael addition and a 6‐endo‐dig cyclization, this cascade reaction allows the modular preparation of highly substituted 6,6‐spiroketals by combining two substrate molecules. Established methods...

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Veröffentlicht in:Advanced synthesis & catalysis 2019-12, Vol.361 (24), p.5605-5615
Hauptverfasser: Ahrens, Alexander, Heinrich, Niklas F., Kohl, Simon R., Hokamp, Martha, Rudolph, Matthias, Rominger, Frank, Hashmi, A. Stephen K.
Format: Artikel
Sprache:eng
Schlagworte:
Alkynes
Cascade chemical reactions
Enones
Functional groups
Michael addition
Silver catalysis
Spiroketals
Substitution reactions
Substrates
Substructures
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Zusammenfassung:A modular synthesis of 6,6‐spiroketals via silver catalysis is reported. By combining an intermolecular Michael addition and a 6‐endo‐dig cyclization, this cascade reaction allows the modular preparation of highly substituted 6,6‐spiroketals by combining two substrate molecules. Established methods accessing this interesting substructure are complemented by this new transformation. The protocol tolerates diverse substitution patterns and functional groups.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.201900988