Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization

Enantioselective One-Pot Organocatalytic Michael Addition/Gold-Catalyzed Tandem Acetalization/Cyclization

Au‐rganocatalytic reaction: A one‐pot process consisting of a Michael addition to a nitroenyne and a subsequent acetalization/cyclization is reported (see scheme; TMS=trimethylsilyl), which results in the formation of nitro‐substituted tetrahydrofuranyl ethers with high diastereo‐ and enantioselecti...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2009-01, Vol.48 (47), p.8923-8926
Hauptverfasser: Belot, Sébastien, Vogt, Kim A, Besnard, Céline, Krause, Norbert, Alexakis, Alexandre
Format: Artikel
Sprache:eng
Schlagworte:
cyclization
gold
heterocycles
Michael addition
organocatalysis
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Zusammenfassung:Au‐rganocatalytic reaction: A one‐pot process consisting of a Michael addition to a nitroenyne and a subsequent acetalization/cyclization is reported (see scheme; TMS=trimethylsilyl), which results in the formation of nitro‐substituted tetrahydrofuranyl ethers with high diastereo‐ and enantioselectivities. Organocatalysis and gold catalysis are compatible and complementary in a one‐pot process.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200903905