Superacid counteranion as flexible-coordinating ligand for asymmetric organo-bismuth catalysis

Jin Hyun Park, Seok Yeol Yoo, Myoung Hyeon Shin, Sungwook Jeong, Yoonsu Park () and Han Yong Bae ()
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Jin Hyun Park: Sungkyunkwan University
Seok Yeol Yoo: Korea Advanced Institute of Science and Technology (KAIST)
Myoung Hyeon Shin: Sungkyunkwan University
Sungwook Jeong: Korea Advanced Institute of Science and Technology (KAIST)
Yoonsu Park: Korea Advanced Institute of Science and Technology (KAIST)
Han Yong Bae: Sungkyunkwan University

Nature Communications, 2025, vol. 16, issue 1, 1-13

Abstract: Abstract Asymmetric binary catalysis, particularly combining chiral Brønsted acids with Lewis acids, is an emerging strategy in synthetic chemistry. Although a few catalyst combinations exist for stereoselective transformations, their scope is generally limited to pre-organized, activated substrates. Here, we report binary catalysis combining an organosuperacid with bismuth, where the counteranion of chiral N-triflyl phosphoramide acts as a flexible-coordinating ligand. This system demonstrates exceptional reactivity and enantioselectivity in the asymmetric allylation of α-keto thioesters, forming enantio-enriched α-hydroxy thioesters with a tetra-substituted stereogenic carbon center (up to > 99% yield and 97% ee). The success is attributed to bismuth’s flexibility during activation, enhancing also interactions with the thioester-tethered substrate. Integrated experimental, analytical, and computational studies highlight the unique assembly enabled by the chiral Brønsted acid and bismuth salt system.

Date: 2025
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DOI: 10.1038/s41467-025-61265-4

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