Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons

Abstract

An asymmetric intramolecular reductive coupling of bisimines has been accomplished for the first time under mild conditions with bis((+)-pinanediolato)diboron as the template, providing the unprecedented chiral dihydrophenanthrene-9,10-cis-diamines in high yields and excellent enantioselectivities. The chiral exocyclic cis-diamine products have served as effective chiral ligands for asymmetric catalysis. A DFT study highlights the crucial roles of the uncommon twisted-boat pathway (instead of the common chair type) and the steric effect in exclusively forming the cis-diamines and achieving high enantioselectivity. This reductive coupling protocol represents a significant expansion of the diboron-promoted [3,3]-sigmatropic rearrangement.

Graphical abstract: Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons

Supplementary files

Article information

Article type
Edge Article
Submitted
20 May 2025
Accepted
17 Jun 2025
First published
17 Jun 2025
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., 2025, Advance Article

Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons

T. Chen, H. Wang, R. Xu, G. Xu, H. Yang, J. Sun, L. W. Chung and W. Tang, Chem. Sci., 2025, Advance Article , DOI: 10.1039/D5SC03633J

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