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

Article Article scientifique Article Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives eng 2020 author Brun Elodie 659907 author Zhang Kefeng 919159 author Guenee Laure 115015 author Lacour Jérôme 0000-0001-6247-8059 99165 250-254 10.1039/C9OB02375E 1477-0520 http://xlink.rsc.org/?DOI=C9OB02375E 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). Dewey 540 36 Département de chimie organique 141 40 Département de chimie minérale, analytique et appliquée 145 false 760 Groupe Lacour Organic and Biomolecular Chemistry 18 2 a742768d-e0ac-42a7-9579-c662bb5f9740 Article (Published version) Public c9ob02375e.pdf 1431161 application/pdf CC BY-NC openAccess Faculté des sciences / Section de chimie et biochimie / Département de chimie organique Faculté des sciences / Section de chimie et biochimie / Département de chimie minérale, analytique et appliquée

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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	Organic and Biomolecular Chemistry			2020	540	215

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Brun, Elodie