Diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis

Lei Dai, Xueting Zhou, Jiami Guo, Xuan Dai, Qingqin Huang and Yixin Lu ()
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Lei Dai: National University of Singapore
Xueting Zhou: National University of Singapore
Jiami Guo: National University of Singapore
Xuan Dai: National University of Singapore
Qingqin Huang: National University of Singapore
Yixin Lu: National University of Singapore

Nature Communications, 2023, vol. 14, issue 1, 1-9

Abstract: Abstract The C−N axially chiral N-arylpyrrole motifs are privileged scaffolds in numerous biologically active molecules and natural products, as well as in chiral ligands/catalysts. Asymmetric synthesis of N-arylpyrroles, however, is still challenging, and the simultaneous creation of contiguous C−N axial and central chirality remains unknown. Herein, a diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis has been developed. The key transformation is a one-pot, three-component oxo-diarylation reaction, which simultaneously creates a C−N axial chirality and a central quaternary stereogenic center. A broad range of unactivated alkynes were readily employed as a reaction partner in this transformation, and the N-arylpyrrole products are obtained in good yields, with excellent enantioselectivities and very good diastereoselectivities. Notably, the N-arylpyrrole skeletons represent interesting structural motifs that could be used as chiral ligands and catalysts in asymmetric catalysis.

Date: 2023
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DOI: 10.1038/s41467-023-40491-8

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