Rhodium(II)/Chiral Phosphoric Acid-Cocatalyzed Enantioselective O-H Bond Insertion of α-Diazo Esters

被引：62

作者：

Zhang, Yiliang ^{[1
,2
]}

Yao, Yuan ^{[1
]}

He, Li ^{[1
,2
]}

Liu, Yang ^{[1
]}

Shi, Lei ^{[1
,2
,3
]}

机构：

[1] Harbin Inst Technol, Sch Chem & Chem Engn, MIIT Key Lab Crit Mat Technol New Energy Convers, Harbin 150001, Heilongjiang, Peoples R China

[2] Harbin Inst Technol, Shenzhen Grad Sch, Shenzhen 518055, Peoples R China

[3] Jingchu Univ Technol, Hubei Key Lab Drug Synth & Optimizat, Jingmen 448000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2017年 / 359卷 / 16期

关键词：

asymmetric catalysis; chiral phosphoric acids; alpha-diazo esters; reaction mechanism; rhodium; CARBENOID INSERTION; EFFICIENT APPROACH; ORGANIC-SYNTHESIS; COMPLEXES; DESIGN; WATER;

D O I：

10.1002/adsc.201700572

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A rhodium(II)/chiral phosphoric acid system has been developed for the asymmetric catalytic insertion of alpha-diazo esters into the O-H bond of carboxylic acids to generate an array of synthetically useful alpha-hydroxy ester derivatives in good ee (up to 95% ee). Furthermore, the substrate scope could be successfully extended to a range of phenols and alcohols with high yield (up to 92%) and excellent enantioselectivity (up to 97%) under mild reaction conditions. Additionally, a density functional theory (DFT) study was performed to elucidate the reaction mechanism.

引用

页码：2754 / 2761

页数：8

共 50 条

[41] Chiral dirhodium(II) catalysts with orthometalated aryl phosphine ligands:: Synthesis and application for enantioselective C-H insertion of α-diazo ketones
Estevan, F
Herbst, K
Lahuerta, P
Barberis, M
Pérez-Prieto, J
ORGANOMETALLICS, 2001, 20 (05) : 950 - 957
[42] A stereospecific access to allylic systems using rhodium(II)-vinyl carbenoid insertion into Si-H, O-H, and N-H bonds
Bulugahapitiya, P
Landais, Y
ParraRapado, L
Planchenault, D
Weber, V
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (06): : 1630 - 1641
[43] Highly Atroposelective Rhodium(II)-Catalyzed N-H Bond Insertion: Access to Axially Chiral N-Arylindolocarbazoles
Ren, Qiao
Cao, Tingting
He, Chunnian
Yang, Meihua
Liu, Haitao
Wang, Lei
ACS CATALYSIS, 2021, 11 (10) : 6135 - 6140
[44] Mechanistic Insights into Asymmetric C-H Insertion Cooperatively Catalyzed by a Dirhodium(II) Complex and Chiral Phosphoric Acid
Liu, Hui
Duan, Jun-Xin
Qu, Deyu
Guo, Li-Ping
Xie, Zhi-Zhong
ORGANOMETALLICS, 2016, 35 (11) : 2003 - 2009
[45] Rhodium-Catalyzed O-H Bond Insertion Reaction between H-Phosphoryl Compounds and 2-Pyridyl Carbenes Generated from Pyridotriazoles
Dong, Chao
Zhang, Can
Wang, Xin
Shen, Ruwei
ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (06) : 1514 - 1522
[46] Diastereoselective access to 2-aminoindanones via the rhodium(ii)-catalyzed tandem reaction involving O-H insertion and Michael addition
Xing, Siyang
Xia, Hanyu
Wang, Xin
Wu, Die
Xu, Xinrui
Su, Yunran
Wang, Kui
Zhu, Bolin
Guo, Junshuo
ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (17) : 3121 - 3126
[47] Insertion of O-H bond of Rh(II)-methylene carbene into alcohols: A stepwise mechanism more plausible than a concerted mechanism
Liu Zhen-feng
Wang Yong
Yue Xian-fang
Han Ke-li
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2007, 23 (02) : 221 - 225
[48] Carboxylic Acid O-H Insertion Reaction of fl-Ester Diazos Enabling Synthesis of fl-Acyloxy Esters
Li, Ziyi
Yao, Xinyu
Zhang, Xin
Mei, Haibo
Han, Jianlin
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (22): : 15483 - 15491
[49] Overcoming O-H Insertion to Para-Selective C-H Functionalization of Free Phenols: Rh(II)/Xantphos Catalyzed Geminal Difunctionalization of Diazo Compounds
Yang, Yang
Lu, Bin
Xu, Guiqing
Wang, Xiaoming
ACS CENTRAL SCIENCE, 2022, 8 (05) : 581 - 589
[50] Enantioselective aza-Friedel-Crafts reaction of furan with α-ketimino esters induced by a conjugated double hydrogen bond network of chiral bis(phosphoric acid) catalysts
Hatano, Manabu
Okamoto, Haruka
Kawakami, Taro
Toh, Kohei
Nakatsuji, Hidefumi
Sakakura, Akira
Ishihara, Kazuaki
CHEMICAL SCIENCE, 2018, 9 (30) : 6361 - 6367

← 1 2 3 4 5 →