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Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives

Published inOrganic and Biomolecular Chemistry, vol. 18, no. 2, p. 250-254
Publication date2020
Abstract

Double hydrothiolation of bis enol ether macrocycles was achieved under photo-mediated conditions. The thiol–ene reactions afford a fully regioselective anti-Markovnikov post-functionalization. Thanks to the use of ethanedithiol as reagent, moderate to excellent diastereoselectivity was accomplished leading to macrocycles containing four defined stereocenters in only three steps from 1,4-dioxane, tetrahydrofuran (THF) or tetrahydropyran (THP).

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BRUN, Elodie et al. Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives. In: Organic and Biomolecular Chemistry, 2020, vol. 18, n° 2, p. 250–254. doi: 10.1039/C9OB02375E
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ISSN of the journal1477-0520
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Creation01/06/2020 10:24:00 AM
First validation01/06/2020 10:24:00 AM
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