Stereoselective tandem cascade furan cycloadditions.
Oligofurans linked by a rigid tether undergo tandem cycloaddition reactions with high stereoselectivity. The reaction of bisfurans with dimethyl acetylenedicarboxylate (DMAD) involves tandem [4 + 2]/[4 + 2] cycloadditions in a pincer mode. The reaction of oligofurans with arynes involves stereoselective tandem [4 + 2]/[4 + 2] cycloaddition reactions in a domino mode. The corresponding aryne adducts have been transformed into extended perylene derivatives by deoxygenation and aromatization with HCl/EtOH.
Departamento de Química Orgánica and Centro de Investigación en Química Biolóxica e Materiais Moleculares (CIQUS), Universidade de Santiago de Compostela , Santiago de Compostela 15782 Spain.
Alejandro
A
Criado
Manuel
M
Vilas-Varela
Agustín
A
Cobas
Dolores
D
Pérez
Diego
D
Peña
Enrique
E
Guitián