The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics

Authors
Ichikawa, J Fujiwara, M Wada, Y Okauchi, T Minami, T
Citation
J. Ichikawa et al., The nucleophilic 5-endo-trig cyclization of gem-difluoroolefins with homoallylic functional groups: syntheses of ring-fluorinated dihydroheteroaromatics, CHEM COMMUN, (19), 2000, pp. 1887-1888
Citations number
36
Categorie Soggetti
Chemistry
Journal title
CHEMICAL COMMUNICATIONS
ISSN journal
13597345 → ACNP
Issue
19
Year of publication
2000
Pages
1887 - 1888
Database
ISI
SICI code
1359-7345(2000):19<1887:TN5COG>2.0.ZU;2-U
Abstract
gem-Difluoroolefins bearing homoallylic tosylamido, hydroxy, or mercapto gr oups undergo intramolecular nucleophilic substitution of the nitrogen, oxyg en, 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 yi elds.