Bifunctional Thiourea-Ammonium Salt Catalysts Derived from Cinchona Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective Aza-Henry Reaction of Ketimines

Bifunctional Thiourea-Ammonium Salt Catalysts Derived from Cinchona Alkaloids: Cooperative Phase-Transfer Catalysts in the Enantioselective Aza-Henry Reaction of Ketimines
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DOI:
10.1021/acs.joc.7b03078
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发表时间:
2018-02-02
影响因子:
3.6
通讯作者:
Duan, Haifeng
Duan, Haifeng
中科院分区:
化学2区
文献类型:
--
作者:
Lu, Ning;Fang, Yanhong;Duan, Haifeng

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以奎宁为原料,合成了硫脲-铵盐双功能相转移催化剂,实现了芳基α-酮酯衍生的酮亚胺的aza-Henry反应。研究了多种芳基α-酮酯衍生的N-Ts酮亚胺,并且以高至优异的产率(高达99%)和良好至高的对映选择性(高达> 99%ee)获得了相应的产物。
An efficient enantioselective aza-Henry reaction of aryl alpha-ketoester-derived ketimines has been realized by using bifunctional thiourea-ammonium salt phase-transfer catalysts, which were derived from quinine. A variety of aryl alpha-ketoester-derived N-Ts ketimines were investigated, and the corresponding products were obtained in high to excellent yields (up to 99%) with good to high enantioselectivities (up to >99% ee).