206. Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives
     Elodie Brun, Ke-Feng Zhang, Laure Guénée, Jérôme Lacour
     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 

open archive unige:128309