Light-Driven Intramolecular Cyclopropanation of Alkene-Tethered N‑Tosylhydrazones: Synthesis of Fused-Cyclopropane γ‑Lactones

Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report the light-driven intramolecular cyclopropanation of alkene-tethered N-tosylhydrazones in the presence of Cs2CO3 and visible l...

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Veröffentlicht in:Organic letters 2024-07, Vol.26 (28), p.6035-6040
Hauptverfasser: Yamini, Pokhriyal, Babbar, Akanksha, Yadagiri, Dongari
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Sprache:eng
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Zusammenfassung:Fused-cyclopropane ring-containing γ-lactone compounds are versatile building blocks in many fields, including the synthesis of biologically active compounds. Here, we report the light-driven intramolecular cyclopropanation of alkene-tethered N-tosylhydrazones in the presence of Cs2CO3 and visible light. We have synthesized various electronically and sterically substituted and heterocyclic-containing fused-(spiro)­cyclopropane γ-lactone compounds in good yields under transition metal-free conditions using a radical-free approach. In addition, the one-pot synthesis of fused-cyclopropane γ-lactones from α-ketoesters and their synthetic utility are also presented.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/acs.orglett.4c02182