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2022 , Vol. 42 >Issue 10: 3221 - 3239

DOI: https://doi.org/10.6023/cjoc202207045

综述与进展

二酮的不对称催化还原反应研究进展

  • 张宇轩 ,
  • 许立民 ,
  • 卢岩 ,
  • 张兆国
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  • 上海交通大学化学化工学院 上海 200240

收稿日期: 2022-07-30

  修回日期: 2022-08-20

  网络出版日期: 2022-09-02

基金资助

国家自然科学基金(22071151)

收起

Progress in Asymmetric Catalytic Reduction of Diketones

  • Yuxuan Zhang ,
  • Limin Xu ,
  • Yan Lu ,
  • Zhaoguo Zhang
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  • School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240
* Corresponding authors. E-mail: ;
E-mail:

Received date: 2022-07-30

  Revised date: 2022-08-20

  Online published: 2022-09-02

Supported by

National Natural Science Foundation of China(22071151)

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摘要

手性二醇类化合物是一类重要的手性结构单元和手性中间体, 过渡金属催化的二酮类化合物的不对称氢化和氢转移反应是获得手性二醇最为直接高效的方法之一. 同时, 手性羟基酮作为二酮的不对称单还原产物, 也广泛应用于手性片段的构建, 其中环状二酮的去对称化甚至可一步构建多个手性中心. 从不同底物类型(1,2-/1,3-/1,4-)的二酮角度出发, 综述了近几十年来二酮类化合物的不对称氢化和氢转移反应研究进展, 着重讨论底物与催化剂配位模式对反应选择性的影响, 并对该领域未来的挑战和发展方向进行了展望.

关键词： 手性二醇; 手性羟基酮; 二酮类化合物; 不对称氢化; 不对称氢转移; 配位模式

本文引用格式

张宇轩 , 许立民 , 卢岩 , 张兆国 . 二酮的不对称催化还原反应研究进展[J]. 有机化学, 2022 , 42(10) : 3221 -3239 . DOI: 10.6023/cjoc202207045

Abstract

Chiral diols are an integral part of chiral building blocks and synthetic intermediates. Transition metal-catalyzed asymmetric hydrogenation and transfer hydrogenation of diketones are recognized as one of the most straightforward and efficient methods for the preparation of enantiomerically enriched diols. Meanwhile, the mono-reduction product of diketones, chiral hydroxyketones, has wide application in chiral fragment construction as well, among which, desymmetrization of cyclic diketones possesses the capability of establishing multiple chiral centers in one step. In this paper, research progress of asymmetric hydrogenation and transfer hydrogenation of diketone compounds in recent decades is reviewed from the perspective of different substrate types (1,2-/1,3-/1,4-diketones), with emphasis on the influence of coordination mode between substrate and catalyst species on the stereoselectivity. In addition, future challenges and development tendencies in this field are summarized and prospected.

Key words： chiral diols; chiral hydroxyketone; diketones; asymmetric hydrogenation; asymmetric transfer hydrogenation; coordination mode

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