Synthesis of Spiro[2.2]pentanes and Vinylcyclopropanes Using Sulfones as Carbene Equivalents
Year: 2025
Type: article
Abstract: ), which makes them intriguing functional groups for medicinal chemistry campaigns. The high degree of strain present in these compounds, however, precludes the use of traditional cyclopropanation methodologies for the synthesis of densely functionalized spiropentane derivatives, making them difficult to obtain. Herein, we report a strategy for the synthesis of substituted arylspiro[2.2]pentanes (16 examples, 24-81% isolated yield) using sulfones as carbene equivalents. During the study, an unexpected formal C-H insertion process was observed when utilizing cyclopropyl sulfone anions as cyclopropylidene equivalents (14 examples, 24-79% isolated yield). Deuterium-labeling studies suggest that the vinylcyclopropane products arise from a stepwise addition-elimination/isomerization pathway.
Source: Organic Letters
Institution: University of North Carolina at Chapel Hill
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: green
Awards: MRI: Acquisition of a 600 MHz Spectrometer with Cryogenic Probe, G2924956855, MRI: Upgrade of a 600 MHz Spectrometer for high-sensitivity Nuclear Magnetic Resonance (NMR), MRI: Acquisition of a Mass Spectrometer, G3981648682, G4108146759, G4513771819, Graduate Research Fellowship Program (GRFP), G5824488030, G6339851269, G8083375506
OpenAlex ID: W4412366834