大学化学 >> 2023, Vol. 38 >> Issue (5): 119-123.doi: 10.3866/PKU.DXHX202206101

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金属异头碳效应

李懿伦, 张香归, 袁耀锋(), 叶克印()   

  • 收稿日期:2022-06-29 录用日期:2022-08-25 发布日期:2022-09-05
  • 通讯作者: 袁耀锋,叶克印 E-mail:yaofeng_yuan@fzu.edu.cn;kyye@fzu.edu.cn

Metallo-Anomeric Effect

Yilun Li, Xianggui Zhang, Yaofeng Yuan(), Keyin Ye()   

  • Received:2022-06-29 Accepted:2022-08-25 Published:2022-09-05
  • Contact: Yaofeng Yuan, Keyin Ye E-mail:yaofeng_yuan@fzu.edu.cn;kyye@fzu.edu.cn

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摘要：

异头碳效应是有机化学中经典立体电子效应的重要组成部分。异头碳效应可以解释吡喃糖中异头碳上电负性较大的取代基倾向于占据直立键，而非立体位阻更具优势的平伏键的现象。本文简要回顾了异头碳效应的发展历史及其重要应用，重点介绍了有机糖化学前沿的金属异头碳效应。当吡喃糖中异头碳上连接金属元素时，可以通过改变金属的种类、价态、配体以及底物结构有效调控金属异头碳效应。通过科研反哺本科教学，有助于化学相关专业学生进一步加深对金属异头碳效应这一新兴研究领域的理解和认识。

关键词: 邻位交叉效应, 异头碳效应, 立体电子效应, 构象

Abstract:

The anomeric effect, one of the classic stereoelectronic effects in organic chemistry, describes the preference of an electronegative substituent at the anomeric carbon of glycosides to adopt the axial configuration. Herein, we briefly survey the history and broad applications of the anomeric effect in organic synthesis. Particularly, we highlight the recent investigations on the related metallo-anomeric effect in carbohydrate chemistry and the possible strategies for its easy regulation via the alteration of the metal, oxidation state, ligand, and structure of the substrate. A positive interplay between scientific research and organic chemistry teaching would profoundly help students to understand the basic concepts and advanced applications of the metallo-anomeric effect.

Key words: Gauche effect, Anomeic effect, Stereoelectronic effect, Conformation