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Acidity-Directed Synthesis of Substituted γ-Butyrolactones from Aliphatic Aldehydes

P. Veeraraghavan Ramachandran* and Debarshi Pratihar

*Department of Chemistry, Purdue University, 560 Oval Drive, West Lafayette, Indiana 47907-2084, Email: chandranpurdue.edu

P. V. Ramachandran, D. Pratihar, Org. Lett., 2007, 9, 2087-2090.

DOI: 10.1021/ol0705806 (free Supporting Information)



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Abstract

Depending on the strength of a Lewis or Brønsted acid catalyst, borate intermediates resulting from the crotylboration of aliphatic aldehydes with ester-containing crotylboronates form either γ-substituted-α-alkylidene-γ-butyrolactones via oxonia cope rearrangement-lactonization or β,γ-disubstituted-α-methylene-γ-butyrolactones via lactonization.

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Key Words

Lactones, Cope Rearrangement


ID: J54-Y2007-1650