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

[1] CHIRAL PHOSPHINOARYLDIHYDROOXAZOLES AS LIGANDS IN ASYMMETRIC CATALYSIS - PD-CATALYZED ALLYLIC SUBSTITUTION
VONMATT, P
PFALTZ, A
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (04): : 566 - 568
[2] New enantioselective chiral imidazolidine ligands for Pd-catalyzed asymmetric allylic alkylation
Lee, EK
Kim, SH
Jung, BH
Ahn, WS
Kim, GJ
TETRAHEDRON LETTERS, 2003, 44 (09) : 1971 - 1974
[3] Synthesis of chiral 1′-substituted oxazolinylferrocenes as chiral ligands for Pd-catalyzed allylic substitution reactions
Park, J
Quan, Z
Lee, S
Ahn, KH
Cho, CW
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1999, 584 (01) : 140 - 146
[4] Highly enantioselective Pd-catalyzed allylic alkylation using new chiral ferrocenylphosphinoimidazolidine ligands
Jin, MJ
Takale, VB
Sarkar, MS
Kim, YM
CHEMICAL COMMUNICATIONS, 2006, (06) : 663 - 664
[5] First chiral phosphoroamidite-phosphite ligands for highly enantioselective and versatile Pd-catalyzed asymmetric allylic substitution reactions
Raluy, Eva
Claver, Carmen
Pamies, Oscar
Dieguez, Montserrat
ORGANIC LETTERS, 2007, 9 (01) : 49 - 52
[6] Polymer-supported chiral phosphinooxazolidine ligands for Pd-catalyzed asymmetic allylic substitution
Kim, YM
Jin, MJ
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2005, 26 (03) : 373 - 374
[7] Asymmetric synthesis of axially chiral anilides by Pd-catalyzed allylic substitutions with P/olefin ligands
Liu, Yilin
Feng, Xiangqing
Du, Haifeng
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (01) : 125 - 132
[8] Pd-catalyzed enantioselective synthesis of axially chiral alkylidene cycloalkanes
Shao, Bing-ru
Jiang, Wen-feng
Zheng, Chao
Shi, Lei
CHEM CATALYSIS, 2023, 3 (07):
[9] Axially Chiral N,N-Ligand-Promoted Pd-Catalyzed Enantioselective Allylic Amination and Alkylation
Liu, Miaomiao
Zhang, Xiaotao
Bao, Rongrong
Xiao, Fangtao
Cen, Shouyi
Zhang, Zhipeng
ORGANIC LETTERS, 2023, 25 (32) : 5946 - 5950
[10] Enantioselective palladium catalyzed allylic substitution with chiral pyridine ligands
Chelucci, G
Caria, V
Saba, A
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 130 (1-2) : 51 - 55

← 1 2 3 4 5 →