A two-step, formal [4 + 2] approach toward piperidin-4-ones via Au catalysis.
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.
Cui
Li
L
Department of Chemistry/216, University of Nevada, Reno, 1664 North Virginia Street, Reno, Nevada 89557, USA.
Peng
Yu
Y
Zhang
Liming
L
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
D000470:Alkaloids; D000588:Amines; D006574:Heterocyclic Compounds, 2-Ring; D007659:Ketones; D010880:Piperidines; C518697:cermizine C; D006046:Gold