Asymmetric Synthesis of Azahelicenes via CPA-Catalyzed Kinetic Resolution

被引：2

作者：

Liu, Wei-Ming ^{[1
,2
]}

Hao, Yong-Jiu ^{[1
,2
]}

Zhang, Yuan ^{[1
,2
]}

Li, Xian-Gao ^{[1
,2
]}

Ji, Shun-Jun ^{[1
,2
]}

Cai, Zhong-Jian ^{[1
,2
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

[2] Soochow Univ, Collaborat Innovat Ctr Suzhou Nano Sci & Technol, Suzhou 215123, Peoples R China

来源：

ORGANIC LETTERS | 2024年 / 27卷 / 01期

基金：

中国国家自然科学基金;

关键词：

ONE HUNDRED YEARS; TRANSFER HYDROGENATION; STEREOSELECTIVE SYNTHESES; SILICON TETRACHLORIDE; HANTZSCH ESTERS; QUINOLINES; EPOXIDES;

D O I：

10.1021/acs.orglett.4c04350

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The azahelicenes are structurally fascinating and practically useful chiral scaffolds, but their synthesis, especially in a catalytically asymmetric manner, is rather challenging. Herein, we report a CPA-catalyzed transfer hydrogenation process, which enables a rapid kinetic resolution of aza[6]helicenes. The established strategy provides facile access to enantioenriched aza[6]helicenes and tetrahydro[6]helicenes from easily available starting materials. A gram-scale reaction and facile conversion of the helical products into a promising chiral Lewis base catalyst, a chiroptical switch material, and monophosphine ligands further highlight the potential application of this protocol.

引用

页码：363 / 368

页数：6

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