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

doi:10.6023/cjoc202204058

有机化学 ›› 2022, Vol. 42 ›› Issue (10): 3405-3418.DOI: 10.6023/cjoc202204058 上一篇下一篇

所属专题：不对称催化专辑

研究论文

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

范铃洁^a, 周涛^b^,^*(), 杨旭^c, 江梦雪^c, 胡信全^a, 史炳锋^*^,^b()

a 浙江工业大学化学工程学院杭州 310032
b 浙江大学化学系前瞻技术研究中心杭州 310027
c 五邑大学生物科技与大健康学院广东江门 529020

收稿日期:2022-04-24 修回日期:2022-05-08 发布日期:2022-11-02
通讯作者: 周涛, 史炳锋
作者简介:
†共同第一作者.
基金资助:
国家自然科学金(21925109); 国家自然科学金(21801223); 浙江省自然科学基金(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

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

Lingjie Fan^a, Tao Zhou^b(), Xu Yang^c, Mengxue Jiang^c, Xinquan Hu^a, Bingfeng Shi^b()

a College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310032
b Center of Chemistry for Frontier Technologies, Department of Chemistry, Zhejiang University, Hangzhou 310027
c School of Biotechnology and Health Sciences, Wuyi University, Jiangmen, Guangdong 529020

Received:2022-04-24 Revised:2022-05-08 Published:2022-11-02
Contact: Tao Zhou, Bingfeng Shi
About author:
†These authors contributed equally to this work.
Supported by:
National Natural Science Foundation of China(21925109); National Natural Science Foundation of China(21801223); Zhejiang Provincial Natural Science Foundation of China(LD22B030003); Open Research Fund of School of Chemistry and Chemical Engineering of Henan Normal University; Center of Chemistry for Frontier Technologies of Zhejiang University

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摘要/Abstract

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.

关键词: 动力学拆分, 碳氢键活化, 不对称, 手性亚砜

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-pGlu-OH as chiral ligand. This protocol is easy to scale-up and compatible with various acrylates bearing core structures of natural products.

Key words: kinetic resolution, C—H activation, enantioselective, chiral sulfoxide

引用此文

范铃洁, 周涛, 杨旭, 江梦雪, 胡信全, 史炳锋. 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[J]. 有机化学, 2022, 42(10): 3405-3418.

Lingjie Fan, Tao Zhou, Xu Yang, Mengxue Jiang, Xinquan Hu, Bingfeng Shi. Pd(II)-Catalyzed Enantioselective C—H Olefination of 2-(Arylsulfinyl)pyridines through Kinetic Resolution[J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3405-3418.

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Entry	Deviation from standard conditions	ee (Yield)/%			S^e
Entry	Deviation from standard conditions	3aa	1a		S^e
1	None	90 (38)^d		91 (49)^d	60
2	Ag₂CO₃ instead of Ag₃PO₄	95 (34)		56 (60)	68
3	AgNO₃ instead of Ag₃PO₄	92 (44)		34 (28)	33
4	AgOAc instead of Ag₃PO₄	91 (26)		52 (70)	36
5	Toluene instead of ⁱPrOH/toluene	90 (34)		34 (63)	26
6	^tBuOH instead of ⁱPrOH/toluene	92 (39)		84 (51)	64
7	ⁱPrOH instead of ⁱPrOH/toluene	94 (43)		78 (52)	77
8	MeOH instead of ⁱPrOH/toluene	95 (32)		43 (63)	60
9	50 ℃ instead of 55 ℃	95 (48)		80 (50)	96
10	No L-pGlu-OH	n.r.

Entry	Deviation from standard conditions	ee (Yield)/%			S^e
Entry	Deviation from standard conditions	3aa	1a		S^e
1	None	90 (38)^d		91 (49)^d	60
2	Ag₂CO₃ instead of Ag₃PO₄	95 (34)		56 (60)	68
3	AgNO₃ instead of Ag₃PO₄	92 (44)		34 (28)	33
4	AgOAc instead of Ag₃PO₄	91 (26)		52 (70)	36
5	Toluene instead of ⁱPrOH/toluene	90 (34)		34 (63)	26
6	^tBuOH instead of ⁱPrOH/toluene	92 (39)		84 (51)	64
7	ⁱPrOH instead of ⁱPrOH/toluene	94 (43)		78 (52)	77
8	MeOH instead of ⁱPrOH/toluene	95 (32)		43 (63)	60
9	50 ℃ instead of 55 ℃	95 (48)		80 (50)	96
10	No L-pGlu-OH	n.r.

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

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