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Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds.

ABSTRACT: The selective assembly of the 1,4-oxathiin nucleus has been treated as a powerful strategy to access this scaffold present in molecules with very interesting properties. In this study, the chameleon-like reactivity of pyridinium 1,4-zwitterionic thiolates is exploited to assemble the 1,4-oxathiin core through a [3 + 3] annulation. The optimal annulation partner has been found to be the iodonium ylide of the cyclic 1,3-diketones. The developed protocol allows the synthesis of a variety of bicyclic 1,4-oxathiin derivatives under very mild conditions under copper(I) iodide catalysis. Access to benzoannulated 1,4-oxathiins has been achieved through iodine-mediated aromatization of the initially obtained bicyclic compounds.

SUBMITTER: Diaz-Jimenez A

PROVIDER: S-EPMC10334467 | biostudies-literature | 2023 Jul

REPOSITORIES: biostudies-literature

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Copper(I) Iodide Catalyzed [3 + 3] Annulation of Iodonium Ylides with Pyridinium 1,4-Zwitterionic Thiolates for the Synthesis of 1,4-Oxathiin Scaffolds.

Díaz-Jiménez Àlex À Kennington Stuart C D SCD Roglans Anna A Pla-Quintana Anna A

Organic letters 20230626 26

The selective assembly of the 1,4-oxathiin nucleus has been treated as a powerful strategy to access this scaffold present in molecules with very interesting properties. In this study, the chameleon-like reactivity of pyridinium 1,4-zwitterionic thiolates is exploited to assemble the 1,4-oxathiin core through a [3 + 3] annulation. The optimal annulation partner has been found to be the iodonium ylide of the cyclic 1,3-diketones. The developed protocol allows the synthesis of a variety of bicycli ...[more]

PMID: 37358369

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