Unexpected ring-opening reactions of aziridines with aldehydes catalyzed by nucleophilic carbenes under aerobic conditions.
[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.
Liu
Yan-Kai
YK
Key Laboratory of Drug-Targeting of Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China.
Li
Rui
R
Yue
Lei
L
Li
Bang-Jing
BJ
Chen
Ying-Chun
YC
Wu
Yong
Y
Ding
Li-Sheng
LS
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
D000447:Aldehydes; D001388:Aziridines; D006838:Hydrocarbons; C030011:carbene; D008697:Methane