Stereoselective synthesis of heterocyclic cage compounds by domino conjugate additions.
Heterocyclic cage compounds have been stereoselectively synthesized from enantiopure [(S)R]-[(p-tolylsulfinyl)methyl]-p-quinols or their amine analogues and 2-(trimethylsilyloxy)furan in the presence of Bu4NF. The method is particularly valuable not only because of the stereochemical control but also because the reactions occur in an experimentally simple one-pot procedure through a domino sequence of three consecutive conjugate additions. The intermediate 1,4-adducts could be isolated when the reaction was carried out in the presence of BF3 x OEt2.
Carreño
M Carmen
MC
Departamento de Química Orgánica (C-I), Universidad Autónoma, Cantoblanco, Madrid, Spain. carmen.carrenno@uam.es
Luzón
Carmen García
CG
Ribagorda
María
M