Visible-Light-Mediated Formal Carbene Insertion Reaction: Enantioselective Synthesis of 1,4-Dicarbonyl Compounds Containing All-Carbon Quaternary Stereocenter

被引：41

作者：

Zhang, Hua ^{[1
]}

Wang, Zheyuan ^{[1
]}

Wang, Zirui ^{[1
]}

Chu, Yunpeng ^{[1
]}

Wang, Shuncheng ^{[1
]}

Hui, Xin-Ping ^{[1
]}

机构：

[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ACS CATALYSIS | 2022年 / 12卷 / 09期

基金：

中国国家自然科学基金;

关键词：

chiral phosphoric acid; carbene; visible light; 1,4-dicarbonyl compounds; diazoesters; INTERMOLECULAR STETTER REACTION; CHIRAL BRONSTED ACIDS; DIAZO-COMPOUNDS; C-C; FUNCTIONALIZATION; ACTIVATION; TRANSFORMATIONS; CATALYSIS; ALDEHYDES; STRATEGY;

D O I：

10.1021/acscatal.2c00064

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

We developed an efficient visible-light-mediated formal carbene insertion reaction of 1,3-diketones with diazoesters for the construction of enantioenriched 1,4-dicarbonyl compounds with a quaternary carbon center. Combining visible light and a Bronsted acid catalyst, chiral 1,4-dicarbonyl compounds were achieved in good yields with high enantioselectivities by a photochemical carbene transfer protocol.

引用

页码：5510 / 5516

页数：7

共 16 条

[11] Catalytic Enantioselective α-Allylation of Deconjugated Butenolides with Aza-π-allylpalladium 1,4-Dipoles: Access to Optically Pure 2-Piperidones Bearing an All-Carbon Quaternary Stereocenter
Yuan, Shu-Pei
Bao, Qing
Sun, Ting-Jia
Zhao, Jian-Qiang
Wang, Zhen-Hua
You, Yong
Zhang, Yan-Ping
Zhou, Ming-Qiang
Yuan, Wei-Cheng
ORGANIC LETTERS, 2022, 24 (45) : 8348 - 8353
[12] Palladium-Catalyzed Carbene Migratory Insertion/Carbonylation Cascade Reaction: Synthesis of 2-Indolones with a C3 All-Carbon Quaternary Center
Cheng, Ming
Huang, Xiao-Yan
Yang, Fang
Zhao, Dong-Mei
Ji, Kegong
Chen, Zi-Sheng
ORGANIC LETTERS, 2022, 24 (05) : 1237 - 1242
[13] Asymmetric Synthesis of Cyclopentene Compounds Containing All-Carbon Quaternary Stereocenters by (3+2) Cycloaddition and Its Application in the Formal Synthesis of (R)-(-)-Puraquinonic Acid
Oga, Miho
Takamatsu, Yusei
Ogura, Akihiro
Takao, Ken-ichi
JOURNAL OF ORGANIC CHEMISTRY, 2022, 87 (13): : 8788 - 8795
[14] The catalytic enantioselective synthesis of tetrahydroquinolines containing all-carbon quaternary stereocenters via the formation of aza-ortho-xylylene with 1,2-dihydroquinoline as a precursor
Li, Guangxun
Liu, Hongxin
Wang, Yingwei
Zhang, Shiqi
Lai, Shujun
Tang, Ling
Zhao, Jinzhong
Tang, Zhuo
CHEMICAL COMMUNICATIONS, 2016, 52 (11) : 2304 - 2306
[15] Synthesis of 1,4-Dicarbonyl Compounds from Silyl Enol Ethers and Bromocarbonyls, Catalyzed by an Organic Dye under Visible-Light Irradiation with Perfect Selectivity for the Halide Moiety over the Carbonyl Group
Esumi, Naoto
Suzuki, Kensuke
Nishimoto, Yoshihiro
Yasuda, Makoto
ORGANIC LETTERS, 2016, 18 (21) : 5704 - 5707
[16] Catalytic Asymmetric Formal C-C Bond Insertion Reaction of Aldehydes via 1,2-Acyl Shift: Construction of All-Carbon Quaternary Stereocenters with Three Carbonyl Groups
Jeong, Hye-Min
Lee, Jin Won
Kim, Dong Kyu
Ryu, Do Hyun
ACS CATALYSIS, 2024, 14 (01)

← 1 2 →