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A Sequential Acyl Thiol-Ene and Thiolactonization Approach for the Synthesis of δ-Thiolactones

Ruairķ O. McCourt, 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, E. M. Scanlan, Org. Lett., 2019, 21, 3460-3464.

DOI: 10.1021/acs.orglett.9b01271 (free Supporting Information)


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Abstract

A facile and scalable synthesis of δ-thiolactones from inexpensive and readily available γ-unsaturated esters incorporates a radical acyl thiol-ene reaction as the key C-S bond forming step. Cyclization is achieved via a Steglich-type thiolactonization of 5-mercaptopentanoic acids.

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Key Words

S-Heterocycles, Steglich Esterification


ID: J54-Y2019