{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Vidal L"],"funding":["Division of Chemistry","University of Liverpool"],"pagination":["8503-8508"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9706811"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["24(46)"],"pubmed_abstract":["Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that the <i>re</i> face of the olefin preferably attacks an iridium carbene intermediate in an asynchronous concerted step that is independent of the geometry of the olefin."],"journal":["Organic letters"],"pubmed_title":["Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides."],"pmcid":["PMC9706811"],"funding_grant_id":["CHE-1764328"],"pubmed_authors":["Aissa C","Hackett A","Robertson CM","Chen PP","Houk KN","Vidal L","Nicolas E"],"additional_accession":[]},"is_claimable":false,"name":"Enantioselective Intramolecular Iridium-Catalyzed Cyclopropanation of α-Carbonyl Sulfoxonium Ylides.","description":"Enantioselective cyclopropanation of α-carbonyl sulfoxonium ylides (SY) has so far been limited to addition/ring closure reactions on electron-poor olefins. Herein, we report the iridium-catalyzed intramolecular cyclopropanation of SY in the presence of a chiral diene in up to 96% yield and 98% enantioselectivity. Moreover, density functional theory calculations suggest that the <i>re</i> face of the olefin preferably attacks an iridium carbene intermediate in an asynchronous concerted step that is independent of the geometry of the olefin.","dates":{"release":"2022-01-01T00:00:00Z","publication":"2022 Nov","modification":"2025-04-05T09:43:38.934Z","creation":"2025-04-05T09:43:38.934Z"},"accession":"S-EPMC9706811","cross_references":{"pubmed":["36367970"],"doi":["10.1021/acs.orglett.2c03396"]}}