Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols★

doi:10.6023/A23040161

Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (8): 955-966.DOI: 10.6023/A23040161 Previous Articles Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

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铜催化的二醇类化合物对映选择性去对称化反应研究进展^★

鱼章龙^a, 李忠良^b, 杨昌江^c, 顾强帅^b^,^*(), 刘心元^a^,^*()

a 南方科技大学化学系深圳格拉布斯研究院深圳 518055
b 南方科技大学化学系前沿与交叉科学研究院深圳 518055
c 大湾区大学理学院化学系东莞 523000

投稿日期:2023-04-23 发布日期:2023-09-14

作者简介:

鱼章龙, 南方科技大学与哈尔滨工业大学联合培养博士研究生. 2015年本科毕业于兰州大学, 获理学学士学位; 2018年硕士毕业于南方科技大学和哈尔滨工业大学(联合培养), 获理学硕士学位; 2018年至今于南方科技大学化学系刘心元教授课题组攻读博士学位. 主要研究课题为自由基参与的二醇类化合物的去对称化反应.

李忠良, 南方科技大学前沿与交叉科学研究院研究副教授. 2009年毕业于中国科学技术大学, 获学士学位; 2014年毕业于香港大学, 获博士学位, 师从杨丹教授. 2015年加入刘心元教授课题组进行博士后研究, 2017年加入前沿与交叉科学研究院, 任研究助理教授, 2020年11月晋升至研究副教授. 目前研究兴趣为发展不对称催化自由基化学, 构建在医药和材料领域有重要用途的手性化合物.

杨昌江, 大湾区大学理学院化学系特聘研究员、硕士生导师. 2011年本科毕业于湖南师范大学; 2017年毕业于南开大学, 获博士学位, 师从贺峥杰教授; 2017年7月加入刘心元教授课题组开展博士后研究, 2020年进入南方科技大学化学系, 任高级研究学者; 2022年4月加入大湾区大学理学院化学系, 任特聘研究员. 目前研究兴趣为催化不对称合成季碳与杂原子手性中心.

顾强帅, 南方科技大学前沿与交叉科学研究院研究副教授、硕士生导师. 2008至2013年在香港大学化学系攻读博士学位, 此后留组从事博士后研究至2016年(导师: 杨丹教授). 2016年9月开始在南方科技大学化学系开展研究工作, 2017年加入前沿与交叉科学研究院, 任研究助理教授, 2020年11月晋升至研究副教授. 主要从事不对称催化和自由基化学方面的工作.

刘心元, 南方科技大学理学院化学系讲席教授. 国家自然科学基金-杰出青年基金获得者, 国家自然科学基金-优秀青年基金获得者, 入选教育部特聘教授(青年). 2001年本科毕业于安徽师范大学; 2004年毕业于安徽师范大学化学系和上海有机所(联合培养), 获理学硕士学位(导师: 朱仕正研究员和王绍武教授); 2010年毕业于香港大学化学系, 获哲学博士学位(导师: 支志明院士); 2010~2012年香港大学和美国Scripps研究所博士后(导师: 支志明院士和Carlos F. Barbas III教授); 2012年9月入职南方科技大学化学系. 研究兴趣在于发展独特的手性阴离子-金属单电子催化剂新策略, 解决该领域中存在的一系列科学难题, 发展多样的不对称自由基催化化学.

^★庆祝《化学学报》创刊90周年.

基金资助:
项目受国家自然科学基金(22025103); 项目受国家自然科学基金(92256301); 项目受国家自然科学基金(21831002); 项目受国家自然科学基金(22101122); 项目受国家自然科学基金(22001109); 项目受国家自然科学基金(22271133); 项目受国家自然科学基金(22201127); 国家重点研发计划(2021YFF0701604); 国家重点研发计划(2021YFF0701704); 深圳市科技计划(KQTD20210811090112004); 深圳市科技计划(JCYJ20220530115409020)

Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★

Zhanglong Yu^a, Zhongliang Li^b, Changjiang Yang^c, Qiangshuai Gu^b(), Xinyuan Liu^a()

a Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055
b Academy for Advanced Interdisciplinary Studies and Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055
c Department of Chemistry, School of Sciences, Great Bay University, Dongguan 523000

Received:2023-04-23 Published:2023-09-14
Contact: *E-mail: guqs@sustech.edu.cn; liuxy3@sustech.edu.cn
About author:
^★Dedicated to the 90th anniversary of Acta Chimica Sinica.
Supported by:
National Natural Science Foundation of China(22025103); National Natural Science Foundation of China(92256301); National Natural Science Foundation of China(21831002); National Natural Science Foundation of China(22101122); National Natural Science Foundation of China(22001109); National Natural Science Foundation of China(22271133); National Natural Science Foundation of China(22201127); National Key R&D Program of China(2021YFF0701604); National Key R&D Program of China(2021YFF0701704); Shenzhen Science and Technology Program(KQTD20210811090112004); Shenzhen Science and Technology Program(JCYJ20220530115409020)

Enantioselective desymmetrization of diols is an important method for the synthesis of complex enantioenriched alcohols, which has broad application prospects in medicinal chemistry, total synthesis, and materials science. In recent years, the use of copper catalysis to achieve diols’ enantioselective desymmetrization has progressed rapidly because copper is inexpensive and readily available compared with other noble metal catalysts. Besides, copper undergoes a two-electron or single-electron transfer process in the catalytic cycle, and the rich oxidation states of copper provides the opportunity to solve some challenging problems. This review summarizes the research progress in this field according to the types of diols (meso diol and prochiral diol) and reactions together with a brief perspective.

Key words: copper catalysis, desymmetrization, diols, asymmetric catalysis

Cite this article

Zhanglong Yu, Zhongliang Li, Changjiang Yang, Qiangshuai Gu, Xinyuan Liu. Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★[J]. Acta Chimica Sinica, 2023, 81(8): 955-966.

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Fig. & Tab. 32

Figure 1. Enantioselective desymmetrization reaction

Figure 2. Desymmetrization of meso 1,2-diols catalyzed by Cu-dioxazoline catalyst

Figure 3. Desymmetrization of meso 1,2-diols catalyzed by Cu/chiral boron-bridged bisoxazoline ligand

Figure 4. Desymmetrization of meso 1,2-diols catalyzed by Cu/chiral piperazine ligand

Figure 5. Desymmetrization of meso 1,2-diols catalyzed by Cu/chiral bis(imidazoline) ligand

Figure 6. Desymmetrization of meso 1,2-diols catalyzed by Cu/chiral diamine ligands that contain a piperazine core

Figure 7. Desymmetrization of meso 1,2-diols catalyzed by Cu/(＋)- sparteine surrogate chiral diamine

Figure 8. Desymmetric carbamoylation of meso diols catalyzed by Cu/chiral BOX ligand

Figure 9. Desymmetrization of meso diols using 2-pyridyl esters as acylating reagents

Figure 10. Desymmetric tosylation of meso diols catalyzed by Cu/chiral BOX ligand

Figure 11. Desymmetric oxidation of meso diol catalyzed by Cu/chiral BOX ligand

Figure 12. Desymmetric arylation of meso diols catalyzed by Cu/chiral BOX ligand

Figure 13. Desymmetric propargylation of meso diols by Cu/borinic acid dual catalysis

Figure 14. Desymmetrization of 2-amino-1,3-diols catalyzed by Cu/chiral BOX ligand

Figure 15. Desymmetric benzoylation and tosylation catalyzed by Cu/chiral BOX ligand

Figure 16. Cu-catalyzed desymmetric benzoylation of 2-substituted glycerols

Figure 17. Desymmetrization of 2-substituted glycerols catalyzed by Cu/chiral imine ligand and its mechanism

Figure 18. Desymmetric benzoylation of 2-substituted 2-benzamido- 1,3-propanediols catalyzed by Cu/chiral BOX ligand

Figure 19. Asymmetric synthesis of all-carbon quaternary stereocenters catalyzed by Cu/Pybox ligand

Figure 20. Synthesis of chiral oxazolidinones catalyzed by Cu/chiral BOX ligand

Figure 21. Desymmetric carbamoylation of the 1,3-diol catalyzed by Cu/chiral BOX ligand

Figure 22. Desymmetric tosylation of 3,3-bis(hydroxymethyl)oxindole catalyzed by Cu/chiral BOX ligand

Figure 23. Synthesis of optically active oxazolines with a quaternary stereocenter catalyzed by Cu/chiral BOX ligand

Figure 24. Enantioselective desymmetrization of aminotriols catalyzed by Cu/chiral BOX ligand

Figure 25. Oxidative desymmetrization of 2-amino-1,3-diols catalyzed by Cu/BOX ligand

Figure 26. Oxidative desymmetrization of 2-substituted 1,2,3-triols catalyzed by Cu/chiral BOX ligand

Figure 27. Intramolecular desymmetric aryl C—O coupling catalyzed by Cu/chiral diamine ligand

Figure 28. Desymmetric acylation of prochiral 2-sila-1,3-propanediols catalyzed by Cu/chiral pybox ligand

Figure 29. Desymmetrization of prochiral silanediols catalyzed by Cu/chiral diphosphine ligand

Figure 30. Desymmetrization of prochiral olefinic 1,3-diols catalyzed by Cu/chiral phosphoric acid

Figure 31. Desymmetric sulfonylation of alcohols catalyzed by Cu/chiral ligands

Figure 32. Enantioselective desymmetric acylation of diols catalyzed by Cu/chiral sulfonamide ligands

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铜催化的二醇类化合物对映选择性去对称化反应研究进展^★

Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★

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铜催化的二醇类化合物对映选择性去对称化反应研究进展★

Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols★

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铜催化的二醇类化合物对映选择性去对称化反应研究进展^★

Research Progress on Copper-Catalyzed Enantioselective Desymmetrization of Diols^★