{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Sanford AB"],"funding":["Ministry of Education of the People&apos;s Republic of China","National Natural Science Foundation of China","National Institute of General Medical Sciences","Zhejiang University","NIGMS NIH HHS"],"pagination":["5017-5023"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC7864534"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["142(11)"],"pubmed_abstract":["Cross-electrophile coupling reactions of two Csp<sup>3</sup>-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes."],"pmcid":["PMC7864534"],"funding_grant_id":["R01GM100212","21702182","R01 GM100212","2019QNA3009","21873081"],"pubmed_authors":["McGinnis TM","Thane TA","Hong X","Jarvo ER","Chen PP","Sanford AB"],"additional_accession":[]},"is_claimable":false,"name":"Nickel-Catalyzed Alkyl-Alkyl Cross-Electrophile Coupling Reaction of 1,3-Dimesylates for the Synthesis of Alkylcyclopropanes.","description":"Cross-electrophile coupling reactions of two Csp<sup>3</sup>-X bonds remain challenging. Herein we report an intramolecular nickel-catalyzed cross-electrophile coupling reaction of 1,3-diol derivatives. Notably, this transformation is utilized to synthesize a range of mono- and 1,2-disubstituted alkylcyclopropanes, including those derived from terpenes, steroids, and aldol products. Additionally, enantioenriched cyclopropanes are synthesized from the products of proline-catalyzed and Evans aldol reactions. A procedure for direct transformation of 1,3-diols to cyclopropanes is also described. Calculations and experimental data are consistent with a nickel-catalyzed mechanism that begins with stereoablative oxidative addition at the secondary center.","dates":{"release":"2020-01-01T00:00:00Z","publication":"2020 Mar","modification":"2025-04-03T23:47:25.507Z","creation":"2025-04-03T23:47:25.507Z"},"accession":"S-EPMC7864534","cross_references":{"pubmed":["32129601"],"doi":["10.1021/jacs.0c01330"]}}