Asymmetric carbonyl-ene reaction catalyzed by chiral N,N'-dioxide-nickel(II) complex: remarkably broad substrate scope.
Highly enantioselective carbonyl-ene reaction of glyoxal derivatives and glyoxylate with various alkenes was accomplished using a novel nickel(II)-N,N'-dioxide complex under mild conditions, which facilitated the asymmetric synthesis of biologically interesting alpha-hydroxy carbonyl compounds. Various aromatic, aliphatic, and heteroaromatic glyoxal derivatives, as well as glyoxylate, could be tolerated in this system and afforded the corresponding adducts in excellent enantioselectivities (97->99% ee) with high yields. Moreover, the catalyst loading could even be decreased to 1 mol%, while the enantioselectivity was basically maintained.
Zheng
Ke
K
Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
Shi
Jian
J
Liu
Xiaohua
X
Feng
Xiaoming
X
D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D010087:Oxides; D009532:Nickel