Base-catalyzed stereoselective vinylation of ketones with arylacetylenes: a new C(sp3)-C(sp2) bond-forming reaction.
Alkylaryl- and alkylheteroarylketones, including those with condensed aromatic moieties, are readily vinylated with arylacetylenes (KOH/DMSO, 100 degrees C, 1 h) to give regio- and stereoselectively the (E)-beta-gamma-ethylenic ketones ((E)-3-buten-1-ones) in 61-84% yields and with approximately 100% stereoselectivity. This vinylation represents a new C(sp(3))-C(sp(2)) bond-forming reaction of high synthetic potential.
Trofimov
Boris A
BA
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences, 1 Favorsky Str., 664033 Irkutsk, Russia. boris_trofimov@irioch.irk.ru
Schmidt
Elena Yu
EY
Ushakov
Igor' A
IA
Zorina
Nadezhda V
NV
Skital'tseva
Elena V
EV
Protsuk
Nadezhda I
NI
Mikhaleva
Al'bina I
AI