Furan-based o-quinodimethanes by gold-catalyzed dehydrogenative heterocyclization of 2-(1-alkynyl)-2-alken-1-ones: a modular entry to 2,3-furan-fused carbocycles.
A strategy for in situ generation of furan-based ortho-quinodimethanes (o-QDMs) by the gold(I)-mediated dehydrogenative heterocyclization of 2-(1-alkynyl)-2-alken-1-ones in the presence of pyridine N-oxide under mild reaction conditions was developed. These in situ furan-based o-QDMs were trapped by electron-deficient olefins and alkynes, thus furnishing various 2,3-furan-fused carbocycles in good yields with high diastereo- and regioselectivities.
Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Department of Chemistry, East China Normal University, 3663 N. Zhongshan Road, Shanghai 200062 (P.R. China) http://faculty.ecnu.edu.cn/s/1811/t/20975/main.jspy.
Liejin
L
Zhou
Mingrui
M
Zhang
Wenbo
W
Li
Junliang
J
Zhang
D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry; D005663:Furans / Q000737:chemistry*; D006046:Gold / Q000737:chemistry*; D006865:Hydrogenation; D015394:Molecular Structure
D003517:Cyclopentanes; D005663:Furans; D006046:Gold; C039281:furan
cycloaddition; gold; heterocycles; nitrogen oxides; synthetic methods