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A New Synthesis of γ-Butyrolactones via AuCl3- or Hg(II)-Catalyzed Intramolecular Hydroalkoxylation of 4-Bromo-3-yn-1-ols

Author:
Reddy, Maddi Sridhar, Kumar, Yalla Kiran, Thirupathi, Nuligonda
Source:
Organic letters 2012 v.14 no.3 pp. 824-827
ISSN:
1523-7052
Subject:
Lewis acids, alcohols, chemical reactions, chemical structure, mercury, regioselectivity, toluene
Abstract:
An efficient conversion of 4-bromo-3-yn-1-ols to γ-butyrolactones via AuCl₃-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.
Agid:
5784865