在铜催化二烷基锌试剂对β-芳基-α,β-不饱和N-对甲苯磺酰基醛亚胺的1,2-加成反应中带有吡啶部分的手性N-杂环卡宾配体
Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines.
作者信息
Soeta Takahiro, Ishizaka Tomohiro, Ukaji Yutaka
机构信息
Division of Material Chemistry, Graduate School of Natural Science and Technology, Kanazawa University , Kakuma, Kanazawa 920-1192, Japan.
出版信息
J Org Chem. 2016 Apr 1;81(7):2817-26. doi: 10.1021/acs.joc.6b00093. Epub 2016 Mar 22.
Asymmetric 1,2-addition of dialkylzinc reagents to α,β-unsaturated N-tosylaldimines was catalyzed by copper salt in the presence of chiral imidazolium salts having a pyridine ring, which were derived from amino acid, to afford the corresponding chiral allylic amines with up to 91% ee in reasonably high yields. The chiral N-heterocyclic carbene (NHC) ligand played an important role in controlling chemoselectivity.
在具有吡啶环的手性咪唑盐（由氨基酸衍生而来）存在下，铜盐催化二烷基锌试剂对α,β-不饱和N-对甲苯磺酰基醛亚胺的不对称1,2-加成反应，以相当高的产率得到相应的手性烯丙基胺，对映体过量值（ee）高达91%。手性N-杂环卡宾（NHC）配体在控制化学选择性方面发挥了重要作用。
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