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Rapid Access to Thiolactone Derivatives through Radical-Mediated Acyl Thiol-Ene and Acyl Thiol-Yne Cyclization

Ruairi O. McCourt, Fabrice Dénès, Goar Sanchez-Sanz and Eoin M. Scanlan*

*Trinity Biomedical Sciences Institute (TBSI), Trinity College Dublin, The University of Dublin, Dublin 2, Ireland, Email: eoin.scanlantcd.ie

R. O. McCourt, F. Dénès, G. Sanchez-Sanz, E. M. Scanlan, Org. Lett., 2018, 20, 2948-2951.

DOI: 10.1021/acs.orglett.8b00996 (free Supporting Information)


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Abstract

Efficient acyl thiol-ene (ATE) or acyl thiol-yne (ATY) cyclization convert unsaturated thiocarboxylic acid derivatives into thiolactones in very good yields under mild conditions. The reactions offer high diastereoselectivity, excellent regiocontrol, and broad substrate scope.

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Key Words

S-heterocycles


ID: J54-Y2018