- Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives
Brun, E.; Zhang, K.-F.; Guénée, L.; Lacour, J.
Org. Biomol. Chem. 2020, 18, 250-254
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).
Supplementary Information (PDF) / Crystal Structure data (CIF)
DOI : 10.1039/C9OB02375E
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