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Efficient Catalytic Enantioselective Hydroxyamination of α-Aryl-α-Cyanoacetates with 2-Nitrosopyridines
Jingchuan Zhang1, Kai Fu1, Lili Lin1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064, P. R. China.
Abstract:
The highly enantioselective totally N-selective hydroxyamination reaction of α-aryl-α-cyanoacetates with 2-nitrosopyridines was realized by using a chiral N,N'-dioxide/Mg(OTf)2 complex as catalyst, which enriches the nitroso chemistry. A variety of 2-cyano-2-[hydroxyl(pyrydin-2-yl)amino]acetates with quaternary stereocenters and potential antibacterial activities were obtained in excellent yields with good to excellent ee values under as low as 0.05 mol % catalyst loading. The products could be easily transformed to useful α-amino amides and 1,2-diamines. Besides, a possible transition state model was proposed to elucidate the origin of the chirality induction.
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