Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines,The Journal of Organic Chemistry

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Chiral NHC Ligands Bearing a Pyridine Moiety in Copper-Catalyzed 1,2-Addition of Dialkylzinc Reagents to β-Aryl-α,β-unsaturated N-Tosylaldimines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2016-03-22 00:00:00 , DOI: 10.1021/acs.joc.6b00093
Takahiro Soeta ₁ , Tomohiro Ishizaka ₁ , Yutaka Ukaji ₁

Affiliation

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.

中文翻译：

在铜催化的1,2-二烷基锌试剂向β-芳基-α，β-不饱和N-甲苯磺酰基亚胺的吡啶催化反应中，带有吡啶基的手性NHC配体

在具有衍生自氨基酸的具有吡啶环的手性咪唑鎓盐的存在下，铜盐催化二烷基锌试剂向α，β-不饱和N-甲苯磺酰基亚胺的不对称1,2-加成反应，得到相应的手性烯丙基胺高达91％ee，且产量相当高。手性N-杂环卡宾（NHC）配体在控制化学选择性中起着重要作用。

更新日期：2016-03-22

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