Phosphoric acid-catalyzed atroposelective construction of axially chiral arylpyrroles

Lei Zhang, Shao-Hua Xiang, Jun (Joelle) Wang (), Jian Xiao, Jun-Qi Wang and Bin Tan ()
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Lei Zhang: Southern University of Science and Technology
Shao-Hua Xiang: Southern University of Science and Technology
Jun (Joelle) Wang: Southern University of Science and Technology
Jian Xiao: Qingdao Agricultural University
Jun-Qi Wang: Southern University of Science and Technology
Bin Tan: Southern University of Science and Technology

Nature Communications, 2019, vol. 10, issue 1, 1-10

Abstract: Abstract Axially chiral arylpyrroles are key components of pharmaceuticals and natural products as well as chiral catalysts and ligands for asymmetric transformations. However, the catalytic enantioselective construction of optically active arylpyrroles remains a formidable challenge. Here we disclose a highly efficient strategy to access enantioenriched axially chiral arylpyrroles by means of organocatalytic atroposelective desymmetrization and kinetic resolution. Depending on the remote control of chiral catalyst, the arylpyrroles were obtained in high yields and excellent enantioselectivities under mild reaction conditions. This strategy tolerates a wide range of functional groups, providing a facile avenue to approach axially chiral arylpyrroles from simple and readily available starting materials. Selected arylpyrrole products proved to be efficient chiral ligands in asymmetric catalysis and also important precursors for further synthetic transformations into highly functionalized pyrroles with potential bioactivity, especially the axially chiral fully substituted arylpyrroles.

Date: 2019
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DOI: 10.1038/s41467-019-08447-z

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