title: Synthesis of Bridged Cyclopentane Derivatives by Catalytic Decarbonylative Cycloaddition of Cyclobutanones and Olefins.
abstract: Herein, we report an intramolecular rhodium-catalyzed decarbonylative coupling between cyclobutanones and alkenes that proceeds by C-C activation and provides a distinct approach to a diverse range of saturated bridged cyclopentane derivatives. In this reaction, cyclobutanones serve as cyclopropane surrogates, reacting in a formal (4+2-1) transformation. To demonstrate the efficacy of this method, it was applied in a concise synthesis of the antifungal drug Tolciclate.
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas, 78712, USA.|Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA.
authors.forename: Xuan
authors.initials: X
authors.lastname: Zhou
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas, 78712, USA. hayeminko@wku.ac.kr.|Department of Bio-Nano Chemistry, Wonkwang University, 460 Iksandae-ro, Iksan, Jeonbuk, 54538, Republic of Korea. hayeminko@wku.ac.kr.
authors.forename: Haye Min
authors.initials: HM
authors.lastname: Ko
authors.affiliation: Department of Chemistry, University of Texas at Austin, Austin, Texas, 78712, USA. gbdong@uchicago.edu.|Department of Chemistry, University of Chicago, Chicago, Illinois, 60637, USA. gbdong@uchicago.edu.
authors.forename: Guangbin
authors.identifier: 0000-0003-1331-6015
authors.initials: G
authors.lastname: Dong
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D003503:Cyclobutanes / Q000737:chemistry*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure
chemical_list: D000475:Alkenes; D001952:Bridged-Ring Compounds; D003503:Cyclobutanes; D003517:Cyclopentanes
keywords: C−C activation; cycloaddition; cyclobutanones; decarbonylation; rhodium catalysis