{"id":8232,"date":"2024-05-28T11:04:33","date_gmt":"2024-05-28T09:04:33","guid":{"rendered":"https:\/\/www.iadchem.uam.es\/?p=8232"},"modified":"2025-02-26T18:15:26","modified_gmt":"2025-02-26T17:15:26","slug":"bicarbonate-binding-catalysis-for-the-enantioselective-desymmetrization-of-keto-sulfonium-salts","status":"publish","type":"post","link":"https:\/\/www.iadchem.uam.es\/?p=8232","title":{"rendered":"Bicarbonate-Binding Catalysis for the Enantioselective Desymmetrization of Keto Sulfonium Salts"},"content":{"rendered":"

\"\"<\/a><\/p>\n

Title:<\/strong> Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts
\nAuthors:<\/strong> Jos\u00e9 Alem\u00e1n, Jorge Humbr\u00edas-Mart\u00edn, Roberto del R\u00edo-Rodr\u00edguez, Fernando Aguilar-Galindo, Sergio D\u00edaz-Tendero and Jose A. Fern\u00e1ndez-Salas
\nJournal:<\/strong> Nature Communications
\nYear:<\/strong> 2024
\nDOI:<\/strong> 10.1038\/s41467-024-48832-x<\/a><\/p>\n

H<\/span>erein, an enantioselective desymmetrization of cyclic keto sulfonium salts through enantioselective deprotonation\/ring opening process by anion-binding catalysis is presented. We report a squaramide\/HCO3- complex as catalytic active species which is able to stereo-differentiate two enantiomeric protons, triggering the ring opening event taking advantage of the great tendency of sulfonium salts to act as leaving groups. Thus, this desymmetrization methodology give rise to \u03b2-methylsulfenylated sulfa-Michael addition type products with excellent yields and very good enantioselectivities. The bifunctional organocatalyst has been demonstrated to be capable of activating simultaneously the base and the keto sulfonium salt by DFT calculations and experimental proofs.<\/p>\n","protected":false},"excerpt":{"rendered":"

Title: Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts Authors: Jos\u00e9 Alem\u00e1n, Jorge Humbr\u00edas-Mart\u00edn, Roberto del R\u00edo-Rodr\u00edguez, Fernando Aguilar-Galindo, Sergio D\u00edaz-Tendero and Jose A. Fern\u00e1ndez-Salas Journal: Nature Communications Year: 2024 DOI: 10.1038\/s41467-024-48832-x Herein, an enantioselective desymmetrization of cyclic keto sulfonium salts through enantioselective deprotonation\/ring opening process by anion-binding catalysis is presented. We report…<\/p>\n","protected":false},"author":3,"featured_media":8238,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[7,5],"tags":[190,275,277],"class_list":["post-8232","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-articles","category-research-highlights","tag-catalysis","tag-enantioselective","tag-sulfonium-salts","entry"],"yoast_head":"\nBicarbonate-Binding Catalysis for the Enantioselective Desymmetrization of Keto Sulfonium Salts - IAdChem - Institute for Advanced Research in Chemical Sciences<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.iadchem.uam.es\/?p=8232\" \/>\n<meta property=\"og:locale\" content=\"en_US\" \/>\n<meta property=\"og:type\" content=\"article\" \/>\n<meta property=\"og:title\" content=\"Bicarbonate-Binding Catalysis for the Enantioselective Desymmetrization of Keto Sulfonium Salts - IAdChem - Institute for Advanced Research in Chemical Sciences\" \/>\n<meta property=\"og:description\" content=\"Title: Bicarbonate-binding catalysis for the enantioselective desymmetrization of keto sulfonium salts Authors: Jos\u00e9 Alem\u00e1n, Jorge Humbr\u00edas-Mart\u00edn, Roberto del R\u00edo-Rodr\u00edguez, Fernando Aguilar-Galindo, Sergio D\u00edaz-Tendero and Jose A. Fern\u00e1ndez-Salas Journal: Nature Communications Year: 2024 DOI: 10.1038\/s41467-024-48832-x Herein, an enantioselective desymmetrization of cyclic keto sulfonium salts through enantioselective deprotonation\/ring opening process by anion-binding catalysis is presented. 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