Enantioselective formal [2+2] cycloaddition of ketenes with nitroso compounds catalyzed by N-heterocyclic carbenes.
Chiral N-heterocyclic carbenes were found to be efficient catalysts for the formal [2+2] cycloaddition reaction of alkyl(aryl)ketenes and nitroso compounds to give the corresponding 1,2-oxazetidin-3-ones in moderate to good yields with high enantioselectivities. Reductive ring-opening of the oxazetidinones give the corresponding α-hydroxy acid derivatives in good yields.
Wang
Tong
T
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Huang
Xue-Liang
XL
Ye
Song
S
D002384:Catalysis; D003500:Cyclization; D007659:Ketones / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D007659:Ketones; D009603:Nitroso Compounds; C030011:carbene; D008697:Methane