Photo-induced thiol–ene reactions for late-stage functionalization of unsaturated polyether macrocycles: regio and diastereoselective access to macrocyclic dithiol derivatives. Issue 2 (6th December 2019)

• Record Type: Journal Article
• Authors: Brun, Elodie; Zhang, Ke-Feng; Guénée, Laure; Lacour, Jérôme
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 2(2019)
• Page Start: 250
• Page End: 254
• Publication Date: 2019-12-06
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02375e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Stereoselective double hydrothiolation of bis enol ether macrocycles was achieved under photo-mediated conditions. 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).