title: Unexpected ring-opening reactions of aziridines with aldehydes catalyzed by nucleophilic carbenes under aerobic conditions.
abstract: [reaction: see text] The chemoselective ring opening of N-tosyl aziridines with aldehydes catalyzed by an N-heterocyclic carbene was investigated under aerobic conditions. Unexpected carboxylates of 1,2-amino alcohols from the corresponding aldehydes, rather than the acyl anion ring-opened beta-amino ketones, were exclusively obtained. A plausible mechanism for this unprecedented carbene-mediated reaction was also proposed.
authors.affiliation: Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
authors.forename: Yan-Kai
authors.initials: YK
authors.lastname: Liu
authors.forename: Rui
authors.initials: R
authors.lastname: Li
authors.forename: Lei
authors.initials: L
authors.lastname: Yue
authors.forename: Bang-Jing
authors.initials: BJ
authors.lastname: Li
authors.forename: Ying-Chun
authors.initials: YC
authors.lastname: Chen
authors.forename: Yong
authors.initials: Y
authors.lastname: Wu
authors.forename: Li-Sheng
authors.initials: LS
authors.lastname: Ding
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001388:Aziridines / Q000737:chemistry*; D002384:Catalysis; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D001388:Aziridines; D006838:Hydrocarbons; C030011:carbene; D008697:Methane