Gold-catalyzed synthesis of chroman, dihydrobenzofuran, dihydroindole, and tetrahydroquinoline derivatives.
Different furans containing an ynamide or alkynyl ether moiety in the side chain were prepared. The gold-catalyzed transformation of these compounds delivered dihydroindole, dihydrobenzofuran, chroman, and tetrahydroquinoline derivatives at room temperature through very fast reactions. Furthermore, the stabilizing effect of the heteroatom directly attached to the intermediate arene oxides led to highly selective reactions, even in the case of only mono-substituted furans, which is quite different from previous results obtained with non-heteroatom-substituted alkynes.
Hashmi
A Stephen K
AS
Organisch-Chemisches Institut, Ruprecht-Karls-Universität, Heidelberg Im Neuenheimer Feld 270, Heidelberg, Germany. hashmi@hashmi.de
Rudolph
Matthias
M
Bats
Jan W
JW
Frey
Wolfgang
W
Rominger
Frank
F
Oeser
Thomas
T