Organocatalytic asymmetric synthesis of Tröger’s bases

Yu-Wei Li, Nan-Nan Mo, Han Zhang, Jian-Xiao Wu, Tian-Jiao Han, Xiao Xiao, Donghui Wei () and Guang-Jian Mei ()
Additional contact information
Yu-Wei Li: Zhengzhou University
Nan-Nan Mo: Zhengzhou University
Han Zhang: Zhengzhou University
Jian-Xiao Wu: Zhengzhou University
Tian-Jiao Han: Zhengzhou University
Xiao Xiao: Zhejiang University of Technology
Donghui Wei: Zhengzhou University
Guang-Jian Mei: Zhengzhou University

Nature Communications, 2025, vol. 16, issue 1, 1-13

Abstract: Abstract The stereochemical course of nitrogen in tertiary amines has long been overlooked because of the low energy barriers for pyramidal inversion between nitrogen-based conformers. Tröger’s base (TB) is a textbook three-dimensional (3D) molecule with N-centered chirality. Despite the major development of TB chemistry, surprisingly few general strategies are available to access enantioenriched TBs. Here, we report the organocatalytic asymmetric synthesis of TBs via the aminalization of tetrahydrodibenzodiazocines with aromatic aldehydes. This chiral phosphoric acid (CPA)-catalyzed protocol features a broad substrate scope (55 examples), high efficiency (up to 96% yield), and excellent enantioselectivity (up to >99% ee). Density functional theory (DFT) calculations are performed to reveal the reaction mechanism and the origin of the enantioselectivity. The success in preparing TB-polymers and aggregation-induced emission luminogen (AIEgen) demonstrates the potential for widespread applications, especially in the fields of materials science.

Date: 2025
References: View complete reference list from CitEc
Citations:

Downloads: (external link)
https://www.nature.com/articles/s41467-025-61772-4 Abstract (text/html)

Related works:
This item may be available elsewhere in EconPapers: Search for items with the same title.

Export reference: BibTeX RIS (EndNote, ProCite, RefMan) HTML/Text

Persistent link: https://EconPapers.repec.org/RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-61772-4

Ordering information: This journal article can be ordered from
https://www.nature.com/ncomms/

DOI: 10.1038/s41467-025-61772-4

Access Statistics for this article

Nature Communications is currently edited by Nathalie Le Bot, Enda Bergin and Fiona Gillespie

More articles in Nature Communications from Nature
Bibliographic data for series maintained by Sonal Shukla () and Springer Nature Abstracting and Indexing ().