A new synthesis of γ-butyrolactones via AuCl(3)- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols

A new synthesis of γ-butyrolactones via AuCl(3)- or Hg(II)-catalyzed intramolecular hydroalkoxylation of 4-bromo-3-yn-1-ols

An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl(3)-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with modera...

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Veröffentlicht in:Organic letters 2012-02, Vol.14 (3), p.824-827
Hauptverfasser: Reddy, Maddi Sridhar, Kumar, Yalla Kiran, Thirupathi, Nuligonda
Format: Artikel
Sprache:eng
Schlagworte:
4-Butyrolactone - chemical synthesis
Bromine Compounds - chemistry
Catalysis
Cyclization
Gold Compounds - chemistry
Hydrogenation
Isomerism
Mercury - chemistry
Molecular Structure
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Zusammenfassung:An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl(3)-catalyzed electrophilic cyclization (hydroxyl-assisted regioselective hydration) in wet toluene is described. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive with moderate to excellent yields obtained in all cases.
ISSN:1523-7052
DOI:10.1021/ol2033493