Rational Design of Chiral Tridentate Ligands: Bifunctional Cobalt(II) Complex/Hydrogen Bond for Enantioselective Michael Reactions

被引：23
|
作者：
Wang, Xiao-Bing [1 ]
Tian, Yin [2 ]
Zhou, Li [1 ]
Xie, Ming-Sheng [1 ]
Qu, Gui-Rong [1 ]
Guo, Hai-Ming [1 ]
机构：
[1] Henan Normal Univ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, NMPA Key Lab Res & Evaluat Innovat Drug, Key Lab Green Chem Media & React,Minist Educ,Sch, 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：
ORGANIC LETTERS | 2022年 / 24卷 / 21期
关键词：
CYCLIC 1,3-DICARBONYL COMPOUNDS; SELECTIVE 3+2 CYCLOADDITION; LEWIS-ACID; STRECKER REACTION; IMINO ESTERS; COMPLEXES; CATALYSTS; DIKETONES; LIBRARY;
D O I：
10.1021/acs.orglett.2c01435
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bifunctional chiral tridentate bis(pyrroloimidazolone)pyridine (PyBPI) ligands have been designed, synthesized, and applied in an asymmetric Michael addition. With a 0.05 mol % PyBPI-Co(II) complex, beta,gamma-unsaturated alpha-keto esters reacted with 4-hydroxycoumarin to give the adducts in 93-99% yields and 90-97% ee. Experiments and DFT calculations supported the dual activation manner, in which the tridentate ligand coordinated with Co(II) to activate the keto ester, and the hydroxyl and carbonyl groups in PyBPI interacted with 4-hydroxycoumarin via two different H bonds.
引用
收藏
页码：3861 / 3866
页数：6
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