Nickel(II)-Catalyzed Asymmetric Inverse-Electron-Demand Diels-Alder Reaction of 2-Pyrones with Styrenes and Indenes

被引：10
作者：
Yu, Heng-Bin [1 ]
Chen, Yang-Guang [1 ]
Tian, Yin [2 ]
Xie, Ming-Sheng [1 ]
Guo, Hai-Ming [1 ]
机构：
[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine C, Sch Chem & Chem Engn, Minist Educ,State Key Lab Antiviral Drugs,Pingyuan, Xinxiang 453007, Henan, Peoples R China
[2] Chengdu Univ Tradit Chinese Med, Sch Pharm, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Peoples R China
来源：
ACS CATALYSIS | 2024年 / 14卷 / 11期
基金：
中国博士后科学基金;
关键词：
asymmetric catalysis; cycloaddition; Diels-Alderreaction; 2-pyrones; styrene; MATCHED; 2-PYRONES; 3+2 CYCLOADDITION; IMINO ESTERS; ALKYLATION;
D O I：
10.1021/acscatal.4c02072
中图分类号：
O64 [物理化学（理论化学）、化学物理学];
学科分类号：
070304 ; 081704 ;
摘要：
With electronically unbiased styrenes and indenes as dienophiles, a highly enantioselective all-carbon-based inverse-electron-demand Diels-Alder reaction of electron-deficient 2-pyrones is reported. Using C-1-symmetric imidazolidine-pyrroloimidazolone pyridine as the tridentate ligand and Ni(OTf)(2) as the Lewis acid, diverse bridged bicyclic lactones were obtained in high yields (88-97% yields), diastereoselectivities (>95:5 dr), and enantioselectivities (90-99% ee). Cyclic enamine and 2,3-dihydrofuran were also suitable dienophiles. DFT calculations supported a concerted [4 + 2] cycloaddition mechanism for the Ni(II) complex-catalyzed reaction with high enantioselectivity caused by steric factors.
引用
收藏
页码：8930 / 8938
页数：9
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