Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols★

doi:10.6023/cjoc202505032

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (9): 3326-3334.DOI: 10.6023/cjoc202505032 Previous Articles Next Articles

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铱/f-Amphox催化吡啶酮的不对称氢化反应制备手性吡啶醇^★

陈奇姝, 杨泊, 稂琪伟, 丁小兵^*(), 李秀秀^*(), 张绪穆^*()

南方科技大学化学系深圳格拉布斯研究院深圳市小分子药物发现与合成重点实验室南方科技大学坪山生物医药研究院广东深圳 518055

收稿日期:2025-05-28 修回日期:2025-07-24 发布日期:2025-08-26
基金资助:
国家重点研发计划(2021YFA1500200); 深圳市基础研究重点(JCYJ20241202125305008)

Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols^★

Qishu Chen, Bo Yang, Qiwei Lang, Xiaobing Ding^*(), Xiuxiu Li^*(), Xumu Zhang^*()

Shenzhen Key Laboratory of Small Molecule Drug Discovery and Synthesis, Shenzhen Grubbs Institute, Department of Chemistry, and Medi-X Pingshan, Southern University of Science and Technology, Shenzhen, Guangdong 518055

Received:2025-05-28 Revised:2025-07-24 Published:2025-08-26
Contact: *E-mail: zhangxm@sustech.edu.cn; lixx7@sustech.edu.cn; dingxb@sustech.edu.cn
About author:
^★ Academic Papers of the 27^th Annual Meeting of the China Association for Science and Technology.
Supported by:
National Key Research and Development Program of China(2021YFA1500200); Shenzhen Key Basic Research Project(JCYJ20241202125305008)

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Abstract

Chiral pyridyl alcohols are a type of synthetically versatile building block for natural products, functional materials and bioactive molecules. Herein, a highly efficient Ir/f-amphox-catalyzed asymmetric hydrogenation of 1-(pyridin-2-yl)ketone derivatives to access chiral pyridyl alcohols was reported. The reaction proceeds smoothly under mild conditions, delivering excellent yields and enantioselectivities (up to >99% ee, turnover number (TON) up to 2000). A broad range of pyridyl alkyl and aryl ketones were successfully transformed, demonstrating the generality and synthetic utility of this methodology.

Key words: asymmetric hydrogenation, f-amphox, pyridyl alcohols

Cite this article

Qishu Chen, Bo Yang, Qiwei Lang, Xiaobing Ding, Xiuxiu Li, Xumu Zhang. Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols^★[J]. Chinese Journal of Organic Chemistry, 2025, 45(9): 3326-3334.

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Fig. & Tab. 5

Scheme 1. Selected bioactive molecules with pyridyl alcohol scaffold

Scheme 2. Asymmetric hydrogenation towards pyridyl alcohols and our approach

Table 1. Effect of ligand and solventa

Table 2. Effect of basea

Table 3. Substrate scope

References 22

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铱/f-Amphox催化吡啶酮的不对称氢化反应制备手性吡啶醇^★

Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols^★

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Abstract

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Fig. & Tab. 5

References 22

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铱/f-Amphox催化吡啶酮的不对称氢化反应制备手性吡啶醇★

Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols★

RichHTML

PDF

Supporting Info.

Knowledge

Abstract

Cite this article

share this article

Fig. & Tab. 5

References 22

Related Articles 15

Recommended Articles

Metrics

Comments

铱/f-Amphox催化吡啶酮的不对称氢化反应制备手性吡啶醇^★

Ir/f-Amphox-Catalyzed Asymmetric Hydrogenation of 1-(Pyridin-2-yl)ketones to Chiral Pyridyl Alcohols^★