RESUMO
Switchable tandem intramolecular aza-Michael/Michael and double aza-Michael reactions allow the oriented synthesis of highly functionalised cyclic skeletons. Conjugate addition of deactivated anilines triggers chemo- and stereo-divergent ring-closure reaction pathways with a striking selectivity depending on reaction conditions.
Assuntos
Ácidos/química , Aminas/química , Compostos Aza/química , Hidrocarbonetos Cíclicos/química , Hidrocarbonetos Cíclicos/síntese química , Catálise , Estrutura Molecular , EstereoisomerismoRESUMO
A wide range of cyclohexadienones has been synthesised in order to study their reactivity and their regio- and stereoselectivity with the enantiopure diene 1 under high-pressure conditions. Computational investigations were used to point out some parameters which affect the reactivity in this high chiral discrimination process. In addition, the resulting [4+2] cycloadducts allowed the preparation of new polyfunctional cyclohexenone derivatives.