Ruthenium-Catalyzed Enantioselective Hydrogenation of 9-Phenanthrols

被引：16

作者：

Zhang, Shu-Xin ^{[1
,2
]}

Xu, Cong ^{[1
]}

Yi, Niannian ^{[1
]}

Li, Shan ^{[1
,2
]}

He, Yan-Mei ^{[1
]}

Feng, Yu ^{[1
,2
]}

Fan, Qing-Hua ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, Beijing 100190, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2022年 / 61卷 / 34期

基金：

国家重点研发计划; 中国国家自然科学基金;

关键词：

9-Phenanthrol; Asymmetric Catalysis; Hydrogenation; Polycyclic Phenols; Ruthenium; ASYMMETRIC TRANSFER HYDROGENATION; SELECTIVE HYDROGENATION; PHYSICOCHEMICAL PROPERTIES; ARENE HYDROGENATION; PHENOL; KETONES; MECHANISM; TAUTOMERIZATION; CYCLOHEXANONE; EQUILIBRIUM;

D O I：

10.1002/anie.202205739

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The enantioselective hydrogenation of arenols to corresponding chiral cyclic alcohols remains a challenge because of their aromaticity and the difficulty in controlling the regio-, chemo-, and stereoselectivity. In this work, the first highly efficient ruthenium-catalyzed enantioselective hydrogenation of 9-phenanthrols has been successfully realized under mild conditions via trapping the unstable keto tautomers. The method provides a facile access to a range of chiral 9,10-dihydrophenanthren-9-ols with up to 98 % yield and >99 % ee. The hydrogenation pathway includes base-promoted tautomerization of 9-phenanthrols and Ru-catalyzed asymmetric hydrogenation of the in situ generated unstable keto tautomers.

引用

页数：6

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