Construction of Tetrahydrofurans by PdII/PdIV-Catalyzed Aminooxygenation of Alkenes

Construction of Tetrahydrofurans by PdII/PdIV-Catalyzed Aminooxygenation of Alkenes

Resolute in the face of elimination: Substituted 3‐aminotetrahydrofurans were prepared in good yield and with modest to high diastereoselectivity by the Pd‐catalyzed reaction shown in the scheme (Phth=phthaloyl). Mechanistic studies indicate a PdII/PdIV catalytic cycle involving cis aminopalladation...

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Veröffentlicht in:Angewandte Chemie International Edition 2007-07, Vol.46 (30), p.5737-5740
Hauptverfasser: Desai, Lopa V., Sanford, Melanie S.
Format: Artikel
Sprache:eng
Schlagworte:
Alkenes - chemistry
allylic compounds
Amination
aminopalladation
Catalysis
Furans - chemistry
Molecular Structure
Octanes - chemistry
oxidation
Oxygen - chemistry
palladium
Palladium - chemistry
Stereoisomerism
tetrahydrofurans
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Zusammenfassung:Resolute in the face of elimination: Substituted 3‐aminotetrahydrofurans were prepared in good yield and with modest to high diastereoselectivity by the Pd‐catalyzed reaction shown in the scheme (Phth=phthaloyl). Mechanistic studies indicate a PdII/PdIV catalytic cycle involving cis aminopalladation and intramolecular CO bond‐forming reductive elimination with retention of configuration at the carbon atom.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200701454