Design, Synthesis, and Structural Analysis of Binaphthyl‐Based Chiral Benzindenes

Chiral benzindenes are an unexplored structural motif in the realm of organic synthesis. This is a result of a lack of synthetic protocols for constructing these compounds in which chirality does not arise from additional chiral substituents. This work introduces an unprecedented route toward chiral benzindenes as a new potential structural motif for further exploratory studies. Starting from readily available ( R )‐BINOL, the convergent synthesis over 9 steps culminated in benzindene with embedded chirality into the binaphthyl framework. The synthetic challenges associated with structural decoration are addressed and evaluated, while DFT and NMR structural analysis of the prepared chiral benzindene revealed its molecular characteristics.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2026-04-24
DOI
https://doi.org/10.1002/adsc.70478
Primary Topic
Synthesis and Properties of Aromatic Compounds
Type
article
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article

Design, Synthesis, and Structural Analysis of Binaphthyl‐Based Chiral Benzindenes

Nikola Topolovčan, Marko Gobin
Advanced Synthesis & Catalysis
Synthesis and Properties of Aromatic Compounds
article

Design, Synthesis, and Structural Analysis of Binaphthyl‐Based Chiral Benzindenes

Nikola Topolovčan, Marko Gobin
article en

Abstract

Chiral benzindenes are an unexplored structural motif in the realm of organic synthesis. This is a result of a lack of synthetic protocols for constructing these compounds in which chirality does not arise from additional chiral substituents. This work introduces an unprecedented route toward chiral benzindenes as a new potential structural motif for further exploratory studies. Starting from readily available ( R )‐BINOL, the convergent synthesis over 9 steps culminated in benzindene with embedded chirality into the binaphthyl framework. The synthetic challenges associated with structural decoration are addressed and evaluated, while DFT and NMR structural analysis of the prepared chiral benzindene revealed its molecular characteristics.

Advanced Synthesis & CatalysisVol. 368(9)
Ruđer Bošković Institute (HR)
Sustainable cities and communities
Openalex Percentile: Top 8%
Synthesis and Properties of Aromatic Compounds
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