title: Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones.
abstract: Control of stereochemistry in photocycloaddition reactions remains a substantial challenge; almost all successful catalytic examples to date have involved [2 + 2] photocycloadditions of enones. We report a method for the asymmetric [3 + 2] photocycloaddition of aryl cyclopropyl ketones that enables the enantiocontrolled construction of densely substituted cyclopentane structures not synthetically accessible using other catalytic methods. These results show that the dual-catalyst strategy developed in our laboratory broadens synthetic chemists' access to classes of photochemical cycloadditions that have not previously been feasible in enantioselective form.
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Adrian G
authors.initials: AG
authors.lastname: Amador
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Evan M
authors.initials: EM
authors.lastname: Sherbrook
authors.affiliation: Department of Chemistry, University of Wisconsin-Madison , 1101 University Avenue, Madison, Wisconsin 53706, United States.
authors.forename: Tehshik P
authors.initials: TP
authors.lastname: Yoon
mesh_terms: D001555:Benzene Derivatives / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D061565:Cycloaddition Reaction; D003503:Cyclobutanes / Q000138:chemical synthesis*; D003521:Cyclopropanes / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry*; D055668:Photochemical Processes; D013237:Stereoisomerism
chemical_list: D001555:Benzene Derivatives; D003503:Cyclobutanes; D003521:Cyclopropanes; D007659:Ketones