Synthesis of Planar Chiral 2-Aryl Aroylferrocenes via PalladiumCatalyzed C-C Bond-Cleavage/Ring-Opening Reaction

被引：5

作者：

Chao, Zengyin ^{[1
]}

Li, Na ^{[1
]}

Hong, Biqiong ^{[2
]}

Ma, Mingming ^{[1
]}

Gu, Zhenhua ^{[1
,2
]}

机构：

[1] Univ Sci & Technol China, Dept Chem, Hefei Natl Lab Phys Sci Microscale, Hefei 230026, Anhui, Peoples R China

[2] Minjiang Univ, Coll Mat & Chem Engn, Fuzhou 350108, Fujian, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 20期

基金：

中国国家自然科学基金;

关键词：

SOLID-STATE CHARACTERIZATION; ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC-SYNTHESIS; KINETIC RESOLUTION; FERROCENE LIGANDS; H ACTIVATION; C(SP(2))-H; CATALYSIS; FUNCTIONALIZATION; DERIVATIVES;

D O I：

10.1021/acs.orglett.1c02775

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A palladium-catalyzed ring-opening reaction of optically active ferrocenyl tertiary alcohols for the construction of planar chiral ketones is reported. The stereochemistry of the hydroxyl group in ferrocenyl alcohols markedly affects reaction: ferrocenyl alcohols with a beta-hydroxyl group show better reactivity and chemoselectivity than the corresponding alpha-hydroxyl analogues. The treatment of alpha-hydroxyl substrates with trifluoroacetic acid successfully realizes the inversion of the orientation of hydroxyl group to the corresponding beta-analogues.

引用

页码：7759 / 7764

页数：6

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