Highly Enantio- and Diastereoselective Synthesis of Tetrahydrofuran Frameworks via Chiral Lewis Acid-Catalyzed Formal [3+2] Cycloaddition of Allylsilanes.

Hosung Lee, Dong Kyu Kim, Pingshan Xin, Jin Won Lee, Terim Seo, Do Hyun Ryu

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Article in Angewandte Chemie (International ed. in English), 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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6 authors.

Hosung LeeDepartment of Chemistry, Sungkyunkwan University, Suwon, South Korea.ORCID https://orcid.org/0009-0000-4540-4349

Dong Kyu KimDepartment of Chemistry, Sungkyunkwan University, Suwon, South Korea.

Pingshan XinDepartment of Chemistry, Sungkyunkwan University, Suwon, South Korea.ORCID https://orcid.org/0009-0006-5316-8466

Jin Won LeeDepartment of Chemistry, Sungkyunkwan University, Suwon, South Korea.ORCID https://orcid.org/0000-0001-7340-1938

Terim SeoDepartment of Chemistry, Sungkyunkwan University, Suwon, South Korea.ORCID https://orcid.org/0009-0009-5152-2048

Do Hyun RyuDepartment of Chemistry, Sungkyunkwan University, Suwon, South Korea.ORCID https://orcid.org/0000-0001-7615-4661

Funding

Higher Education Discipline Innovation Project D18012Korea Basic Science InstituteKorea government 2023-00219859Korea government 2023-00279862Ministry of Education 2022-NF000854Ministry of Education 2022-NF001081Ministry of Education 2025- 02413546National Research Foundation of Korea

6 · The paper itself

Abstract

A formal [3+2] cycloaddition via cyclization/1,2-hydride shift initiated by nucleophilic attack of allylsilanes has been developed for the enantioselective synthesis of cis-2,5-disubstituted tetrahydrofuran-3-ones. In the presence of chiral oxazaborolidinium ion (COBI) catalyst, the reaction proceeded in high yields (up to 88%) with excellent stereoselectivity (up to 99% ee, > 20:1 dr). Key advantages of this approach are its unprecedented ability to forge THF scaffolds asymmetrically without inherent chirality, its high stereoselectivity including cis-selectivity, and its capability to control four stereocenters in a single transformation.

Indexed as

allylsilanesdiastereoselectivityenantioselectivityformal [3+2] cycloadditiontetrahydrofuran

Identifiers

PMID42531031

DOI10.1002/anie.202524631

PMCPMC13592307

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