Design and Synthesis of Diphosphine Ligands Based on the Chiral Biindolyl Scaffold and Their Application in Transition-Metal Catalysis

An extremely concise, scalable, and stereoselective synthesis of a privileged chiral skeleton based on 2,2′-biindolyl and commercially available chiral building blocks has been developed. This novel skeleton allows for easy access to a range of bisphosphine ligands (decagram scale, up to 58% total y...

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Bibliographic Details
Published in:Organic letters 2024-03, Vol.26 (8), p.1623-1628
Main Authors: Zhang, Fuhao, Chen, Gen-Qiang, Zhang, Xumu
Format: Article
Language:English
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Summary:An extremely concise, scalable, and stereoselective synthesis of a privileged chiral skeleton based on 2,2′-biindolyl and commercially available chiral building blocks has been developed. This novel skeleton allows for easy access to a range of bisphosphine ligands (decagram scale, up to 58% total yield, only three steps). The synthetic method is characterized by an efficient central-to-axial chirality transfer strategy. In particular, the superior performance of the ligands has been demonstrated in diverse reactions, including several asymmetric hydrogenations, asymmetric conjugate reductions, and cycloisomerization reactions, indicating a great potential for the application of the newly developed chiral backbones in further modifications and exploration of novel chiral ligands and catalysts.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03068