Organocatalyzed diastereo- and enantioselective synthesis of N–N atropisomeric isoindolinones bearing central chirality

Xingguang Li (), Xin-Ze Wang, Boming Shen, Qian-Yu Chen, Huijing Xiang, Peiyuan Yu () and Pei-Nian Liu ()
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Xingguang Li: East China University of Science and Technology
Xin-Ze Wang: East China University of Science and Technology
Boming Shen: Southern University of Science and Technology
Qian-Yu Chen: East China University of Science and Technology
Huijing Xiang: Shanghai University
Peiyuan Yu: Southern University of Science and Technology
Pei-Nian Liu: East China University of Science and Technology

Nature Communications, 2025, vol. 16, issue 1, 1-11

Abstract: Abstract Methods for catalytically constructing of N–N axially chiral scaffolds have garnered significant attention since such compounds are widely present in natural products, bioactive molecules, and organic materials. Herein, we report a highly diastereoselective and enantioselective organocatalyzed [4 + 1] annulation method for synthesizing diverse valuable isoindolinones that possessing N–N axial and central chiralities. This methodology uses a chiral phosphoric acid as a bifunctional catalyst to promote a cascade sequence involving two nucleophilic additions, dehydration, and dearomatization processes. Control experiments and DFT calculations revealed a possible mechanism in which the stereoselectivity-determining step is likely to involve the irreversible formation of a hydroxy biaryl intermediate. Additionally, preliminary biological activity studies showed that some of these N–N axially chiral isoindolinones have potential in suppressing tumor-cell proliferation.

Date: 2025
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DOI: 10.1038/s41467-025-56838-2

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