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Stereoselective synthesis of 2,3-disubstituted dihydrobenzofuran using alkyne Prins type cyclization to vinylogous carbonates

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Abstract

An intramolecular, alkyne Prins type cyclization of vinylogous carbonates derived from o-alkynyl phenols is developed for the stereoselective construction of trans-2,3-disubstituted dihydrobenzofuran derivatives. Strong Lewis acids like TMSOTf catalyse this reaction efficiently. The presence of mildly electron donating groups on aryl rings increases the efficiency of the reaction.

An intramolecular, alkyne Prins type cyclization of vinylogous carbonates derived from o-alkynyl phenols is developed for the stereoselective construction of trans-2,3-disubstituted dihydrobenzofuran derivatives. Strong Lewis acids like TMSOTf catalyse this reaction efficiently. Presence of mildly electron donating groups on aryl rings increases the efficiency of the reaction.

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  1. Department of Chemistry, Indian Institute of Technology Madras, Chennai, 600036, India

    SANTOSH J GHARPURE & V PRASATH

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GHARPURE, S.J., PRASATH, V. Stereoselective synthesis of 2,3-disubstituted dihydrobenzofuran using alkyne Prins type cyclization to vinylogous carbonates. J Chem Sci 123, 943–949 (2011). https://doi.org/10.1007/s12039-011-0162-8

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