Brønsted acid catalyzed propargylation of 1,3-dicarbonyl derivatives. Synthesis of tetrasubstituted furans.
Simple Brønsted acids such as p-toluenesulfonic acid monohydrate (PTS) efficiently catalyze a direct substitution of the hydroxyl group in propargylic alcohols with 1,3-dicarbonyl compounds. Selective propargylation or allenylation is obtained depending on the nature of the alkynol. Reactions can be performed in air in undried solvents with water being the only side product of the process. By applying this reaction as the key step, a range of interesting polysubstituted furans can easily be synthesized in a one-pot procedure. [reaction: see text].
Sanz
Roberto
R
Departamento de Química, Area de Química OrgAnica, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001-Burgos, Spain. rsd@ubu.es
Miguel
Delia
D
Martínez
Alberto
A
Alvarez-Gutiérrez
Julia M
JM
Rodríguez
Félix
F