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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

Maddi Sridhar Reddy*, Yalla Kiran Kumar and Nuligonda Thirupathi

*Medicinal and Process Chemistry Division, Central Drug Research Institute, CSIR, Lucknow 226 001, India, Email: msreddycdri.res.in

M. S. Reddy, Y. K. Kumar, N. Thirupathi, Org. Lett., 2012, 14, 824-827.

DOI: 10.1021/ol2033493 (free Supporting Information)


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Abstract

AuCl3-catalyzed electrophilic cyclization of 4-bromo-3-yn-1-ols via hydroxyl-assisted regioselective hydration in wet toluene enables the synthesis of  γ-butyrolactones in good yields. Various secondary and tertiary alcohols including benzylic systems were found to be equally reactive.

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Key Words

Lactones


ID: J54-Y2012-0300