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

页码：12732 / 12735

页数：4

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