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

被引：26
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
相关论文
共 49 条
[1]   PyBidine-Cu(OTf)2-Catalyzed Asymmetric [3+2] Cycloaddition with Imino Esters: Harmony of Cu-Lewis Acid and Imidazolidine-NH Hydrogen Bonding in Concerto Catalysis [J].
Arai, Takayoshi ;
Ogawa, Hiroki ;
Awata, Atsuko ;
Sato, Makoto ;
Watabe, Megumi ;
Yamanaka, Masahiro .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (05) :1595-1599
[2]   Chiral Bis(imidazolidine)pyridine-Cu(OTf)2: Catalytic Asymmetric Endo-Selective [3+2] Cycloaddition of Imino Esters with Nitroalkenes [J].
Arai, Takayoshi ;
Mishiro, Asami ;
Yokoyama, Naota ;
Suzuki, Kuniko ;
Sato, Hiroyasu .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (15) :5338-+
[3]   PyBidine/Copper Catalyst: Asymmetric exo′-Selective [3+2] Cycloaddition using Imino Ester and Electrophilic Indole [J].
Awata, Atsuko ;
Arai, Takayoshi .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (39) :10462-10465
[4]   Applications of Pybox Complexes in Asymmetric Catalysis [J].
Babu, Sheba Ann ;
Krishnan, K. Keerthi ;
Ujwaldev, S. M. ;
Anilkumar, Gopinathan .
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 7 (06) :1033-1053
[5]   Svnthesis of a new chiral N,N,N-tridentate pyridinebisimidazoline ligand library and its application in Ru-catalyzed asymmetric epoxidation [J].
Bhor, S ;
Anilkumar, G ;
Tse, MK ;
Klawonn, M ;
Dobler, C ;
Bitterlich, B ;
Grotevendt, A ;
Beller, M .
ORGANIC LETTERS, 2005, 7 (16) :3393-3396
[6]   Catalytic, Asymmetric Michael Reactions of Cyclic Diketones with β,γ-Unsaturated α-Ketoesters [J].
Calter, Michael A. ;
Wang, Jun .
ORGANIC LETTERS, 2009, 11 (10) :2205-2208
[7]   Catalytic asymmetric carbon-carbon bond forming reactions catalyzed by tetrahydroisoquinoline (TIQ) N,N′-dioxide ligands [J].
Cele, Zamani E. D. ;
Sosibo, Sphelele C. ;
Andersson, Pher G. ;
Kruger, Hendrik G. ;
Maguire, Glenn E. M. ;
Govender, Thavendran .
TETRAHEDRON-ASYMMETRY, 2013, 24 (04) :191-195
[8]   Chiral 2,2′-bipyridines, 1,10-phenanthrolines, and 2,2′:6′,2"-terpyridines:: Syntheses and applications in asymmetric homogeneous catalysis [J].
Chelucci, G ;
Thummel, RP .
CHEMICAL REVIEWS, 2002, 102 (09) :3129-3170
[9]   Iminopyridine Oxazoline Iron Catalyst for Asymmetric Hydroboration of 1,1-Disubtituted Aryl Alkenes [J].
Chen, Jianhui ;
Xi, Tuo ;
Lu, Zhan .
ORGANIC LETTERS, 2014, 16 (24) :6452-6455
[10]   Highly Enantioselective Michael Addition of Cyclic 1,3-Dicarbonyl Compounds to β,γ-Unsaturated α-Keto Esters [J].
Chen, Xing-Kuan ;
Zheng, Chang-Wu ;
Zhao, Sheng-Li ;
Chai, Zhuo ;
Yang, Ying-Quan ;
Zhao, Gang ;
Cao, Wei-Guo .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (10) :1648-1652
12345