Article Dans Une Revue Organic Letters Année : 2025

Monobromination of Cubane 1,4-Diester, A Synthetic Handle for Fluorosulfonylation and Giese-type Reactions

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The bromination of cubane 1,4-diester is described for the first time. The versatility of the C–Br bond for forging C–S and C–C bonds was demonstrated. The fluorosulfonylation reaction allowed the first entry of the cubane in click chemistry illustrated with nucleophiles, electrophiles, and alkynes. The grafting of appendages was illustrated with amino acids and dipeptides, enabling the discrimination of the diesters via cyclization into “fused cubane-lactam” structures.

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hal-05033584 , version 1 (14-04-2025)

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Laly Donnier-Valentin, Julien Legros, C. Fressigne, Daniela Vuluga, Bruno Linclau, et al.. Monobromination of Cubane 1,4-Diester, A Synthetic Handle for Fluorosulfonylation and Giese-type Reactions. Organic Letters, In press, ⟨10.1021/acs.orglett.5c00967⟩. ⟨hal-05033584⟩
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