钯催化的不对称碳氢键烯基化动力学拆分2-(芳基亚磺酰基)吡啶  

Pd(II)-Catalyzed Enantioselective C—H Olefination of 2-(Arylsulfinyl)pyridines through Kinetic Resolution

作　　者：范铃洁 周涛 杨旭 江梦雪 胡信全[1] 史炳锋[2] Fan Lingjie;Zhou Tao;Yang Xu;Jiang Mengxue;Hu Xinquan;Shi Bingfeng(College of Chemical Engineering,Zhejiang University of Technology,Hangzhou 310032;Center of Chemistry for Frontier Technologies,Department of Chemistry,Zhejiang University,Hangzhou 310027;School of Biotechnology and Health Sciences,Wuyi University,Jiangmen,Guangdong 529020)

机构地区：[1]浙江工业大学化学工程学院,杭州310032 [2]浙江大学化学系前瞻技术研究中心,杭州310027 [3]五邑大学生物科技与大健康学院,广东江门529020

出　　处：《有机化学》2022年第10期3405-3418,共14页Chinese Journal of Organic Chemistry

基　　金：国家自然科学金(Nos.21925109,21801223);浙江省自然科学基金(No.LD22B030003);河南师范大学化学化工学院开放基金;浙江大学化学前瞻技术研究中心资助项目。

摘　　要：通过发展钯催化的不对称碳氢键烯基化,实现了2-(芳基亚磺酰基)吡啶的动力学拆分.利用该方法,在温和条件下用廉价商业化的L-焦谷氨酸作为手性配体,以较高到优异的产率和对映选择性实现了一系列手性亚砜的合成,对映选择性高达99%,拆分因子s大于200.该方法对于天然产物衍生的丙烯酸酯以及克级制备反应都有很好的兼容性.A Pd(II)-catalyzed enantioselective C—H olefination of 2-(arylsulfinyl)pyridines through kinetic resolution is developed.A wide range of chiral sulfoxides were prepared in good to high yields and selectivity(up to 99%ee,s-factor of up to 200)under mild conditions using cheap and commercially available L-p Glu-OH as chiral ligand.This protocol is easy to scale-up and compatible with various acrylates bearing core structures of natural products.

关 键 词：动力学拆分 碳氢键活化 不对称 手性亚砜 

分 类 号：O626.32[理学—有机化学]