Ligand-controlled divergent asymmetric C(sp3)−H and C(sp3)−O insertion via vinyl cations

Cui-Ting Li, Li-Gao Liu, Jia-Zheng Li, Hao-Xuan Dong, Roman A. Novikov, Ze-Shu Wang (), Xin Hong (), Bo Zhou and Long-Wu Ye ()
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Cui-Ting Li: Xiamen University
Li-Gao Liu: Zhejiang University
Jia-Zheng Li: Xiamen University
Hao-Xuan Dong: Xiamen University
Roman A. Novikov: 47 Leninsky prosp.
Ze-Shu Wang: Xiamen University
Xin Hong: Zhejiang University
Bo Zhou: Xiamen University
Long-Wu Ye: Xiamen University

Nature Communications, 2025, vol. 16, issue 1, 1-12

Abstract: Abstract The insertion of either C−H bond or C−O bond via bond cleavage has proven to be a very attractive strategy for the construction of C−C and C−O bonds in organic synthesis. However, such divergent catalytic asymmetric reactions for the selective formation of C(sp3)−H insertion and formal C(sp3)−O insertion products from the same precursors are rarely explored. Herein, we report a ligand-controlled divergent asymmetric C(sp3)−H insertion and formal C(sp3)−O insertion reaction via vinyl cations by a non-diazo approach, leading to the practical and atom-economical assembly of a range of chiral spiro and fused polycyclic pyrroles in generally moderate to excellent yields with generally excellent chemo- and enantioselectivities. Importantly, this protocol not only represents a rare example of successful ligand-controlled asymmetric divergent insertion reaction, but also constitutes an enantioselective 1,6-C−H insertion and an asymmetric carbenoid insertion into acetals via a non-diazo approach.

Date: 2025
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DOI: 10.1038/s41467-025-59328-7

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