Organocatalytic enantioconvergent α-substitution of sulfonium salts by nitrogen nucleophiles.

Zhiyang Li, Yao Luo, Alex C Bissember, Jianwei Sun

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Article in Chemical science, 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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2 · The registry

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4 · The record

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5 · Who and what money

Authors and funding

4 authors.

Zhiyang LiDepartment of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong SAR 999077 China sunjw@ust.hk.

Yao LuoDepartment of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong SAR 999077 China sunjw@ust.hk.

Alex C BissemberSchool of Natural Sciences - Chemistry, University of Tasmania Hobart Tasmania 7001 Australia.ORCID https://orcid.org/0000-0001-5515-2878

Jianwei SunDepartment of Chemistry and the Hong Kong Branch of Chinese National Engineering Research Centre for Tissue Restoration & Reconstruction, The Hong Kong University of Science and Technology Clear Water Bay Kowloon Hong Kong SAR 999077 China sunjw@ust.hk.ORCID https://orcid.org/0000-0002-2470-1077

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Chiral α-amino carbonyl compounds are essential building blocks in the synthesis of natural products and pharmaceuticals. Direct enantioconvergent nucleophilic substitution represents a powerful approach, but it has not been well established for the synthesis of α-amino ketones. Herein, we report a robust organocatalytic protocol with α-keto sulfonium salts. Utilizing a chiral phosphoric acid (CPA) in an aqueous/organic biphasic system, we achieved enantioconvergent substitution with free amines in high yields and excellent enantioselectivity. Mechanistic studies suggest that the CPA plays a dual role as both the source of chirality and a phase-transfer catalyst, facilitating the reaction

Identifiers

PMID42582904

DOI10.1039/d6sc04100k

PMCPMC13458546

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