Metal-free oxidative cross-coupling enabled practical synthesis of atropisomeric QUINOL and its derivatives

Peng-Ying Jiang, Kai-Fang Fan, Shaoyu Li (), Shao-Hua Xiang and Bin Tan ()
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Peng-Ying Jiang: Southern University of Science and Technology
Kai-Fang Fan: Southern University of Science and Technology
Shaoyu Li: Southern University of Science and Technology
Shao-Hua Xiang: Southern University of Science and Technology
Bin Tan: Southern University of Science and Technology

Nature Communications, 2021, vol. 12, issue 1, 1-9

Abstract: Abstract As an important platform molecule, atropisomeric QUINOL plays a crucial role in the development of chiral ligands and catalysts in asymmetric catalysis. However, efficient approaches towards QUINOL remain scarce, and the resulting high production costs greatly impede the related academic research as well as downstream industrial applications. Here we report a direct oxidative cross-coupling reaction between isoquinolines and 2-naphthols, providing a straightforward and scalable route to acquire the privileged QUINOL scaffolds in a metal-free manner. Moreover, a NHC-catalyzed kinetic resolution of QUINOL N-oxides with high selectivity factor is established to access two types of promising axially chiral Lewis base catalysts in optically pure forms. The utility of this methodology is further illustrated by facile transformations of the products into QUINAP, an iconic ligand in asymmetric catalysis.

Date: 2021
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DOI: 10.1038/s41467-021-22621-2

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