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
收藏
页码：363 / 368
页数：6
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