Asymmetric Allylic C-H Oxidation for the Synthesis of Chromans

被引：124
作者：
Wang, Pu-Sheng [1 ,2 ]
Liu, Peng [1 ,2 ]
Zhai, Yu-Jia [1 ,2 ]
Lin, Hua-Chen [1 ,2 ]
Han, Zhi-Yong [1 ,2 ]
Gong, Liu-Zhu [1 ,2 ,3 ]
机构：
[1] Univ Sci & Technol China, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Peoples R China
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[3] Collaborat Innovat Ctr Chem Sci & Engn, Tianjin, Peoples R China
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2015年 / 137卷 / 40期
关键词：
VITAMIN-E; SECALONIC ACIDS; ENANTIOSELECTIVE APPROACH; TERMINAL OLEFINS; CHIRAL CHROMANS; ALKYLATION; ALCOHOLS; FUNCTIONALIZATION; ALPHA; TETRAHYDROXANTHONE;
D O I：
10.1021/jacs.5b08477
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An enantioselective intramolecular allylic C-H oxidation to generate optically active chromans has been accomplished under the cooperative catalysis of a palladium complex of chiral phosphoramidite ligand and 2-fluorobenzoic acid. Mechanistic studies suggest that this reaction commences with a Pd-catalyzed allylic C-H activation event and then undergoes asymmetric allylic alkoxylation. The synthetic significance of the method has been embodied by concisely building up a key chiral intermediate to access (+)-diversonol.
引用
收藏
页码：12732 / 12735
页数：4
相关论文
共 63 条
[61]   Hybrid-Increased Radical-Scavenging Activity of Resveratrol Derivatives by Incorporating a Chroman Moiety of Vitamin E [J].
Yang, Jie ;
Liu, Guo-Yun ;
Lu, Dong-Liang ;
Dai, Fang ;
Qian, Yi-Ping ;
Jin, Xiao-Ling ;
Zhou, Bo .
CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (43) :12808-12813
[62]   Two new prenylated xanthones and a new prenylated tetrahydroxanthone from the pericarp of Garcinia mangostana [J].
Zhang, Yaozheng ;
Song, Zhijun ;
Hao, Jing ;
Qiu, Shengxiang ;
Xu, Zhifang .
FITOTERAPIA, 2010, 81 (06) :595-599
[63]   Recent development of direct asymmetric functionalization of inert C-H bonds [J].
Zheng, Chao ;
You, Shu-Li .
RSC ADVANCES, 2014, 4 (12) :6173-6214
1234567