Kinetic resolution of heterobiaryl N-oxides by asymmetric C-H olefination: an expeditious access to (R)-QUINAP

被引：4

作者：

Zhang, Qi-Ying ^{[1
]}

Wang, Hai-Yang ^{[1
]}

Wang, Songlin ^{[1
]}

Ma, Jing ^{[1
]}

Guo, Hai-Ming ^{[1
]}

机构：

[1] Henan Normal Univ, Sch Chem & Chem Engn,Minist Educ, Collaborat Innovat Ctr Henan Prov Green Mfg Fine, State Key Lab Antiviral Drugs,Pingyuan Lab,Key La, Xinxiang 453007, Henan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 20期

基金：

中国国家自然科学基金;

关键词：

AXIALLY CHIRAL COMPOUNDS; IAN-AMINES; ALLYLATION; ALDEHYDES; CONSTRUCTION; IODINATION; COMPLEXES; MECHANISM; QUINOX;

D O I：

10.1039/d3qo01083j

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly efficient kinetic resolution of heterobiaryl N-oxides was realized through Pd catalyzed-asymmetric C-H olefination with the s factor of up to 102.7. This new approach offers versatile access to two types of optically active 1-arylisoquinoline N-oxides with excellent ee (up to 97% ee and 99% ee, respectively). Moreover, the recovered arylisoquinoline N-oxides could be transformed into (R)-QUINAP with 92% ee without an external reductant in two steps.

引用

页码：5210 / 5215

页数：6

共 50 条

[21] P(=O)R2-Directed Asymmetric Catalytic C-H Olefination Leading to C-N Axially Chiral Targets
Jin, Shengzhou
Wang, Yu
Yan, Jasmine X.
Xu, Ting
Ning, Min
Yuan, Qingkai
Li, Guigen
ORGANIC LETTERS, 2025, 27 (12) : 2838 - 2844
[22] Aliphatic C-H Functionalization Using Pyridine N-Oxides as H-Atom Abstraction Agents
Schlegel, Marcel
Qian, Siran
Nicewicz, David A.
ACS CATALYSIS, 2022, 12 (16): : 10499 - 10505
[23] Metal-Catalyzed Direct C-H Fluoroalkenylation of Pyridine N-Oxides and Related Derivatives
Lehecq, Alexis
Rousee, Kevin
Schneider, Cedric
Levacher, Vincent
Hoarau, Christophe
Pannecoucke, Xavier
Bouillon, Jean-Philippe
Couve-Bonnaire, Samuel
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (21) : 3049 - 3054
[24] Pd(II)-Catalyzed Enantioselective C-H Olefination of 2-(Arylsulfinyl)pyridines through Kinetic Resolution
Fan, Lingjie
Zhou, Tao
Yang, Xu
Jiang, Mengxue
Hu, Xinquan
Shi, Bingfeng
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (10) : 3405 - 3418
[25] Cu(I)-Catalyzed Highly Regioselective C-H Amidation of Quinoline N-Oxides with Dioxazolones
Ren, Zhiqiang
Feng, Tianhui
Gao, Tianli
Han, Bo
Guo, Ruili
Ma, Haojie
Wang, Ji-Jiang
Zhang, Yuqi
ORGANIC LETTERS, 2024, 26 (40) : 8532 - 8536
[26] Synthesis of 2-Sulfonylthiazoles via Heteroaryl C-H Sulfonylation of Thiazole N-Oxides
Um, Hyun-Suk
Shin, Woong Sik
Son, Kyu Jin
Lee, Chulbom
SYNLETT, 2023, 34 (12) : 1447 - 1451
[27] C-H functionalization of quinoline N-oxides catalyzed by Pd(ii) complexes: a computational study
Costa, Paulo J.
Martins, Frederico F.
Pi, Chao
Cui, Xiuling
Calhorda, Maria Jose
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2023, 25 (34) : 22755 - 22767
[28] Palladium-Catalyzed Enantioselective C-H Olefination of Diaryl Sulfoxides through Parallel Kinetic Resolution and Desymmetrization
Zhu, Yu-Chao
Li, Yan
Zhang, Bo-Chao
Zhang, Feng-Xu
Yang, Yi-Nuo
Wang, Xi-Sheng
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (18) : 5129 - 5133
[29] Rh(III)-catalyzed chemoselective C-H functionalizations of tertiary aniline N-oxides with alkynes
Huang, Xiaolei
Liang, Wenbo
Shi, Yang
You, Jingsong
CHEMICAL COMMUNICATIONS, 2016, 52 (37) : 6253 - 6256
[30] Site-Selective C-H Alkylation of Diazine N-Oxides Enabled by Phosphonium Ylides
Ghosh, Prithwish
Kwon, Na Yeon
Han, Sangil
Kim, Saegun
Han, Sang Hoon
Mishra, Neeraj Kumar
Jung, Young Hoon
Chung, Sang J.
Kim, In Su
ORGANIC LETTERS, 2019, 21 (16) : 6488 - 6493

← 1 2 3 4 5 →