title: A two-step, formal [4 + 2] approach toward piperidin-4-ones via Au catalysis.
abstract: An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstrated in a highly diastereoselective synthesis of (+/-)-cermizine C.
authors.affiliation: Department of Chemistry/216, University of Nevada, Reno, 1664 North Virginia Street, Reno, Nevada 89557, USA.
authors.forename: Li
authors.initials: L
authors.lastname: Cui
authors.forename: Yu
authors.initials: Y
authors.lastname: Peng
authors.forename: Liming
authors.initials: L
authors.lastname: Zhang
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis*; D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry; D006574:Heterocyclic Compounds, 2-Ring / Q000138:chemical synthesis*; D007659:Ketones / Q000138:chemical synthesis*; D010880:Piperidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D000588:Amines; D006574:Heterocyclic Compounds, 2-Ring; D007659:Ketones; D010880:Piperidines; C518697:cermizine C; D006046:Gold