title: Asymmetric carbonyl-ene reaction catalyzed by chiral N,N'-dioxide-nickel(II) complex: remarkably broad substrate scope.
abstract: 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.
authors.affiliation: Key Laboratory of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, PR China.
authors.forename: Ke
authors.initials: K
authors.lastname: Zheng
authors.forename: Jian
authors.initials: J
authors.lastname: Shi
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D002384:Catalysis; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D010087:Oxides; D009532:Nickel