The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics
- 18 September 2000
- journal article
- Published by Royal Society of Chemistry (RSC) in Chemical Communications
- No. 19,p. 1887-1888
- https://doi.org/10.1039/b004978f
Abstract
gem-Difluoroolefins bearing homoallylic tosylamido, hydroxy, or mercapto groups undergo intramolecular nucleophilic substitution of the nitrogen, oxygen, or sulfur with loss of fluorine via a 5-endo-trig process, leading to 2-fluoro-2-pyrrolines, 5-fluoro-2,3-dihydrofurans, or -thiophenes in high yields.Keywords
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