Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons

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-<i>cis</i>-diamines in high yields and excellent enantioselectivities. The chiral exocyclic <i>cis</i>-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 <i>cis</i>-diamines and achieving high enantioselectivity. This reductive coupling protocol represents a significant expansion of the diboron-promoted [3,3]-sigmatropic rearrangement.

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Publication Details

Journal
Chemical Science
Published
2025-01-01
DOI
https://doi.org/10.1039/d5sc03633j
Primary Topic
Organoboron and organosilicon chemistry
Type
article
Field-Weighted Citation Impact
0.00

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article

Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons

Jiangtao Sun, Lung Wa Chung, Wenjun Tang, Haoyang Wang et al.
Chemical Science
Organoboron and organosilicon chemistry
article

Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons

Jiangtao Sun, Lung Wa Chung, Wenjun Tang, Haoyang Wang, Chen Tian, Ronghua Xu, He Yang, Guangqing Xu
article en

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-<i>cis</i>-diamines in high yields and excellent enantioselectivities. The chiral exocyclic <i>cis</i>-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 <i>cis</i>-diamines and achieving high enantioselectivity. This reductive coupling protocol represents a significant expansion of the diboron-promoted [3,3]-sigmatropic rearrangement.

Chemical ScienceVol. 16(29)
Southern University of Science and Technology (CN), Shanghai Institute of Organic Chemistry (CN), Changzhou University (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, Science and Technology Commission of Shanghai Municipality, Youth Innovation Promotion Association of the Chinese Academy of Sciences, Southern University of Science and Technology, Guangdong Provincial Key Laboratory Of Catalysis, National Key Research and Development Program of China, Youth Innovation Promotion Association
Openalex Percentile: Top 89%
Organoboron and organosilicon chemistry
DOIOpen Access PDFOpenAlex
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Asymmetric intramolecular reductive coupling of bisimines templated by chiral diborons — Jiangtao Sun, Lung Wa Chung, et al. · Chemical Science (2025) | TGRS Research Map | TGRS