Catalytic Atroposelective Electrophilic Amination of Indoles

Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N‐sulfonyl‐3‐arylaminoindoles with excellent optical purity. This reaction was furnished by 1,6‐nucleophilic addition to p‐quinone diimines. Control experiments suggest...

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Published in:Angewandte Chemie 2022-08, Vol.134 (31), p.n/a
Main Authors: Qin, Jingyang, Zhou, Tong, Zhou, Tai‐Ping, Tang, Langyu, Zuo, Honghua, Yu, Huaibin, Wu, Guojiao, Wu, Yuzhou, Liao, Rong‐Zhen, Zhong, Fangrui
Format: Article
Language:English
Subjects:
Amination
Anticancer properties
Atroposelectivity
Chemistry
Computer applications
Conjugation
C−N Axis
Heterocycles
Indoles
Quinones
Selectivity
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Summary:Reported here is the first catalytic atroposelective electrophilic amination of indoles, which delivers functionalized atropochiral N‐sulfonyl‐3‐arylaminoindoles with excellent optical purity. This reaction was furnished by 1,6‐nucleophilic addition to p‐quinone diimines. Control experiments suggest an ionic mechanism that differs from the radical addition pathway commonly proposed for 1,6‐addition to quinones. The origin of 1,6‐addition selectivity was investigated through computational studies. Preliminary studies show that the obtained 3‐aminoindoles atropisomers exhibit anticancer activities. This method is valuable with respect to enlarging the toolbox for atropochiral amine derivatives. The atroposelective electrophilic amination of indoles catalyzed by a chiral phosphoric acid (CPA) is reported. The reaction proceeds by asymmetric 1,6‐addition to p‐quinone diimines to deliver atropochiral N‐sulfonyl‐3‐arylaminoindoles in good yields and with excellent ee values.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.202205159