Issue 29, 2023
From the journal:

Chemical Science

Catalytic asymmetric indolization by a desymmetrizing [3 + 2] annulation strategy†

Changhui Wu, ORCID logo a   Zhiqian Chang,a   Chuanyong Peng,a   Chen Bai,a   Junhao Xinga  and  Xiaowei Dou ORCID logo *ab  

* Corresponding authors

a Department of Chemistry, School of Science, China Pharmaceutical University, Nanjing, P. R. China
E-mail: dxw@cpu.edu.cn

b State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing, P. R. China

Abstract

A new catalytic asymmetric indolization reaction by a desymmetrizing [3 + 2] annulation strategy is developed. The reaction proceeds via a rhodium-catalyzed enantioposition-selective addition/5-exo-trig cyclization/dehydration cascade between ortho-amino arylboronic acids and 2,2-disubstituted cyclopentene-1,3-diones to produce N-unprotected cyclopenta[b]indoles bearing an all-carbon quaternary stereocenter in high yields with good enantioselectivities. A quantitative structure–selectivity relationship (QSSR) model was established to identify the optimal chiral ligand, which effectively controlled the formation of the stereocenter away from the reaction site. Density functional theory (DFT) calculations, non-covalent interaction analysis, and Eyring analysis were performed to understand the key reaction step and the function of the ligand.

Graphical abstract: Catalytic asymmetric indolization by a desymmetrizing [3 + 2] annulation strategy

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Article information

DOI
https://doi.org/10.1039/D3SC02474A
Article type
Edge Article
Submitted
16 May 2023
Accepted
28 Jun 2023
First published
29 Jun 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2023,14, 7980-7987

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Catalytic asymmetric indolization by a desymmetrizing [3 + 2] annulation strategy

C. Wu, Z. Chang, C. Peng, C. Bai, J. Xing and X. Dou, Chem. Sci., 2023, 14, 7980 DOI: 10.1039/D3SC02474A

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