An alternate approach for the synthesis of 1,3-dihydroisobenzofurans has been explored by the addition of nucleophiles to an activated a-keto ester (1 ). This addition results in an intramolecular cyclization with the ortho benzyllic bromide, which rapidly yields the desired 1,3-dihydroisobenzofuran substructure 2  in high yields (>95%). We are examining this cyclization reaction to determine its scope and limitation. Specifically, the reactivity with various nucleophiles and the characterization of these cyclization reactions will be presented.

Formation of 1,3-dihydroisobenzofurans by intramolecular cyclization reactions

243rd National Meeting (2012)

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