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 |
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Format: | Artikel |
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. |
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ISSN: | 1523-7060 1523-7052 1523-7052 |
DOI: | 10.1021/acs.orglett.4c02182 |