Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene

doi:10.6023/cjoc202306006

Chinese Journal of Organic Chemistry ›› 2023, Vol. 43 ›› Issue (12): 4239-4250.DOI: 10.6023/cjoc202306006 Previous Articles Next Articles

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Quinim配体的探索及其在镍催化烯烃的不对称胺甲酰基-烷基化反应的应用

吴利城, 伍贤青^*(), 曲景平, 陈宜峰^*()

华东理工大学化学与分子工程学院费林加诺贝尔奖科学家联合研究中心材料生物学与动态化学前沿科学中心上海 200237

收稿日期:2023-06-10 修回日期:2023-07-10 发布日期:2023-07-27
基金资助:
国家自然科学基金(22171079); 上海市自然科学基金(21ZR1480400); 上海市启明星项目(20QA1402300); 上海市科技重大专项(2018SHZDZX03); 高等学校学科创新引智计划(B16017); 中国博士后科学基金(2021M701197); 上海市扬帆项目(23YF1408800); 中央高校基本科研专项基金资助项目

Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene

Licheng Wu, Xianqing Wu^*(), Jingping Qu, Yifeng Chen^*()

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237

Received:2023-06-10 Revised:2023-07-10 Published:2023-07-27
Contact: *E-mail: xianqingwu@ecust.edu.cn;yifengchen@ecust.edu.cn
Supported by:
National Natural Science Foundation of China(22171079); Natural Science Foundation of Shanghai(21ZR1480400); Shanghai Rising-Star Program(20QA1402300); Shanghai Municipal Science and Technology Major Project(2018SHZDZX03); Program of Introducing Talents of Discipline to Universities(B16017); China Postdoctoral Science Foundation(2021M701197); Shanghai Sailing Program(23YF1408800); Fundamental Research Funds for the Central Universities

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Abstract

The development of new chiral ligand constitutes the cornerstone of asymmetric catalysis. An asymmetric synthesis of α,α-dialkylated pyrrolidinones enabled by Ni-catalyzed reductive carbamoyl-alkylation of 1,1-disubstituted alkene- tethered carbamoyl chlorides and primary alkyl iodides is presented. After extensive investigation of Quinim ligands, it is found that the evolution of chiral ligand ^p^-tolQuinim to ^1-NapQuinim is critical for formation of the all-carbon quaternary center in high yield and enantioselectivity and broad functional group tolerance. The newly developed catalytic system that combines nickel salts and the ^1-NapQuinim ligand also improves both the yield and enantioselectivity in the synthesis of α-monoalkylated γ-lactams.

Key words: Quinim ligand, nickel catalysis, quaternary stereocenters, γ-lactam

Cite this article

Licheng Wu, Xianqing Wu, Jingping Qu, Yifeng Chen. Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene[J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4239-4250.

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Quinim配体的探索及其在镍催化烯烃的不对称胺甲酰基-烷基化反应的应用

Exploration of Quinim Ligand in Ni-Catalyzed Enantioselective Reductive Carbamoyl-Alkylation of Alkene

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