Development of Axially Chiral Pyridylidene Amine Ligands and their Application in Pd-Catalyzed Enantioselective Allylic Substitution

被引：0

作者：

Chen, Zhikang ^{[1
]}

Liu, Jiahao ^{[1
]}

Ou, Weiying ^{[1
]}

Kato, Terumasa ^{[1
,2
,3
]}

Wang, Zhe ^{[1
,2
]}

Chen, Yong ^{[4
]}

Liu, Yan ^{[1
,2
]}

Maruoka, Keiji ^{[1
,2
,3
]}

机构：

[1] Guangdong Univ Technol, Sch Chem Engn & Light Ind, Guangzhou 510006, Peoples R China

[2] Guangdong Univ Technol, Guangdong Prov Key Lab Plant Resources Biorefinery, Guangzhou 510006, Peoples R China

[3] Kyoto Univ, Grad Sch Pharmaceut Sci, Lab Organocatalyt Chem, Sakyo, Kyoto 6068501, Japan

[4] China Natl Anal Ctr, Guangzhou 510070, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 17期

基金：

中国国家自然科学基金;

关键词：

BIS(OXAZOLINE) LIGANDS; BOND STANNYLATION; SN BONDS; PALLADIUM; COMPLEXES; ALKYLATION; DESIGN; SWITCH;

D O I：

10.1021/acs.joc.4c01334

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of novel axially chiral pyridylidene amine (PYE) ligands has been developed, and their catalytic capability has been demonstrated in various highly efficient and enantioselective Pd-catalyzed asymmetric allylic substitutions. A density-functional theory (DFT) study explains the preferential enantiocontrol in the key transition states of the axially chiral PYE ligand-promoted Pd-catalyzed allylic alkylation.

引用

页码：12800 / 12811

页数：12

共 50 条

[41] Chiral P,N,N-Ligands for Pd-Catalyzed Asymmetric Allylic Substitutions
Qin Hao
Hou Chuanjin
Liang Dinghua
He Xinwei
Li Ling
Hu Xiangping
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (01) : 282 - 290
[42] Simple chiral sulfinyl imine-thioether ligands for Pd-catalyzed allylic alkylation
You, Ge-Yun
Liu, Xiao-Feng
Fang, Pei-Wen
Liang, Lu-Fang
Dai, Cheng-Hao
Feng, Bin
CHEMICAL PAPERS, 2022, 76 (07) : 4615 - 4620
[43] Pd-Catalyzed Asymmetric Allylic Etherizations with Oximes by Chiral Alkene-Phosphine Ligands
Cao, Ziping
Liu, Zhaoqun
Liu, Yilin
Du, Haifeng
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (15): : 6401 - 6406
[44] New types of soluble polymer-supported bisphosphine ligands with a cyclobutane backbone for Pd-catalyzed enantioselective allylic substitution reactions
Zhao, DB
Sun, J
Ding, KL
CHEMISTRY-A EUROPEAN JOURNAL, 2004, 10 (23) : 5952 - 5963
[45] Highly enantioselective Pd-catalyzed allylic substitution employing a new chiral phosphine ligand: Kinetic resolution of 3-acetoxycyclohexene.
Zhang, XM
Longmire, JM
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2000, 219 : U133 - U133
[46] Enantioselective Pd-Catalyzed Allylic Substitution using Phosphite-Oxazoline PHOX-Based Ligands containing a Methylene Linker
de la Cruz-Sanchez, Pol
Biosca, Maria
Magre, Marc
Faiges, Jorge
Margalef, Jessica
Pamies, Oscar
Dieguez, Montserrat
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2022, 2022 (10)
[47] Efficient Activation of Allylic Alcohols in Pd-Catalyzed Allylic Substitution Reactions
Ma, Xiantao
Yu, Jing
Wang, Zilong
Zhang, Yun
Zhou, Qiuju
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2020, 40 (09) : 2669 - 2677
[48] Application of mixed phosphorus/sulfur ligands based on terpenoids in Pd-catalyzed asymmetric allylic substitution and Rh-catalyzed hydrogenation
Gavrilov, Konstantin N.
Chuchelkin, Ilya V.
Gavrilov, Vladislav K.
Firsin, Ilya D.
Trunina, Valeria M.
Shiryaev, Alexey A.
Shkirdova, Alena O.
Bermesheva, Evgeniya V.
Tafeenko, Victor A.
Chernyshev, Vladimir V.
Zimarev, Vladislav S.
Goulioukina, Nataliya S.
ORGANIC & BIOMOLECULAR CHEMISTRY, 2024, 22 (31) : 6362 - 6369
[49] Pd-catalyzed enantioselective allylic substitution: New strategic options for the total synthesis of natural products
Graening, T
Schmalz, HG
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (23) : 2580 - 2584
[50] Enantioselective construction of axially chiral cyclohexylidene scaffolds via Pd-catalyzed asymmetric coupling reaction
Ma, Chun
Sun, Yue
Liu, Siyuan
Li, Zhi-Ming
Yang, Junfeng
Guo, Hao
Zhang, Junliang
CHEM CATALYSIS, 2022, 2 (11): : 3196 - 3206

← 1 2 3 4 5 →