Issue 10, 2024
From the journal:

Organic Chemistry Frontiers

Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles†

Xuan Zhang,a   Qi Teng, ORCID logo *a   Yanru Ren,a   Baitong Wei,a   Chen-Ho Tung ORCID logo a  and  Zhenghu Xu ORCID logo *abc  

* Corresponding authors

a Key Lab for Colloid and Interface Chemistry of Education Ministry, School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China
E-mail: xuzh@sdu.edu.cn, qteng@sdu.edu.cn

b State Key Laboratory of Organometallic Chemistry Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, PR China

c Key Laboratory of Precise Synthesis of Functional Molecules of Zhejiang Province, School of Science, Westlake University, No. 18 Shilongshan Road, Hangzhou 310024, China

Abstract

A Rh-catalyzed neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition of 1,6-diynes and ynamides to generate C–N axially chiral indole derivatives has been developed. The notable features of this method include 100% atom-economy, a wide substrate scope and excellent enantioselectivities by using the easily available chiral SEGPHOS ligands.

Graphical abstract: Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles

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Article information

DOI
https://doi.org/10.1039/D4QO00042K
Article type
Research Article
Submitted
08 Jan 2024
Accepted
26 Mar 2024
First published
28 Mar 2024

Org. Chem. Front., 2024,11, 2857-2863

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Neighboring group-directed asymmetric [2 + 2 + 2] cycloaddition to access C–N axially chiral indoles

X. Zhang, Q. Teng, Y. Ren, B. Wei, C. Tung and Z. Xu, Org. Chem. Front., 2024, 11, 2857 DOI: 10.1039/D4QO00042K

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