Organocatalytic diastereo- and atroposelective construction of N–N axially chiral pyrroles and indoles

Shao-Jie Wang, Xia Wang, Xiaolan Xin, Shulei Zhang, Hui Yang, Ming Wah Wong () and Shenci Lu ()
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Shao-Jie Wang: Northwestern Polytechnical University (NPU)
Xia Wang: Northwestern Polytechnical University (NPU)
Xiaolan Xin: Northwestern Polytechnical University (NPU)
Shulei Zhang: Northwestern Polytechnical University (NPU)
Hui Yang: National University of Singapore
Ming Wah Wong: National University of Singapore
Shenci Lu: Northwestern Polytechnical University (NPU)

Nature Communications, 2024, vol. 15, issue 1, 1-13

Abstract: Abstract The construction of N–N axially chiral motifs is an important research topic, owing to their wide occurrence in natural products, pharmaceuticals and chiral ligands. One efficient method is the atroposelective dihydropyrimidin-4-one formation. We present herein a direct catalytic synthesis of N–N atropisomers with simultaneous creation of contiguous axial and central chirality by oxidative NHC (N-heterocyclic carbenes) catalyzed (3 + 3) cycloaddition. Using our method, we are able to synthesize structurally diverse N–N axially chiral pyrroles and indoles with vicinal central chirality or bearing a 2,3-dihydropyrimidin-4-one moiety in moderate to good yields and excellent enantioselectivities. Further synthetic transformations of the obtained axially chiral pyrroles and indoles derivative products are demonstrated. The reaction mechanism and the origin of enantioselectivity are understood through DFT calculations.

Date: 2024
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DOI: 10.1038/s41467-024-44743-z

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