{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Park JW"],"funding":["NIGMS NIH HHS"],"pagination":["3310-3"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC4856524"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["138(10)"],"pubmed_abstract":["We report a Rh-catalyzed enantioselective cycloisomerization of ?,?-heptadienes to afford cyclohexenes bearing quaternary carbon centers. Rhodium(I) and a new SDP ligand promote chemoselective formation of a cyclohex-3-enecarbaldehyde motif that is inaccessible by the Diels-Alder cycloaddition. Various ?,?-bisallylaldehydes rearrange to generate six-membered rings by a mechanism triggered by aldehyde C-H bond activation. Mechanistic studies suggest a pathway involving regioselective carbometalation and endocyclic ?-hydride elimination."],"journal":["Journal of the American Chemical Society"],"pubmed_title":["Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers."],"pmcid":["PMC4856524"],"funding_grant_id":["GM105938","R01 GM105938"],"pubmed_authors":["Park JW","Chen Z","Dong VM"],"additional_accession":[]},"is_claimable":false,"name":"Rhodium-Catalyzed Enantioselective Cycloisomerization to Cyclohexenes Bearing Quaternary Carbon Centers.","description":"We report a Rh-catalyzed enantioselective cycloisomerization of ?,?-heptadienes to afford cyclohexenes bearing quaternary carbon centers. Rhodium(I) and a new SDP ligand promote chemoselective formation of a cyclohex-3-enecarbaldehyde motif that is inaccessible by the Diels-Alder cycloaddition. Various ?,?-bisallylaldehydes rearrange to generate six-membered rings by a mechanism triggered by aldehyde C-H bond activation. Mechanistic studies suggest a pathway involving regioselective carbometalation and endocyclic ?-hydride elimination.","dates":{"release":"2016-01-01T00:00:00Z","publication":"2016 Mar","modification":"2020-10-31T08:24:27Z","creation":"2019-03-27T02:13:02Z"},"accession":"S-EPMC4856524","cross_references":{"pubmed":["26953640"],"doi":["10.1021/jacs.6b01445"]}}