In this paper, Paolo Melchiorre’s research group merges iminium ion catalysis with the concept of vinylogy, resulting in the transmission of the LUMO-lowering activating effect through a conjugated pi-system.
They present a catalytic asymmetric 1,6-addition of alkyl thiols to cyclic dienones via vinylogous iminium ion catalysis and they obtain the δ-functionalised desired compounds with high stereocontrol and good site-selectivity.
This catalytic route is considered one of most significant recent developments and future trends in synthetic chemistry and it has been reported in Synfacts.
Aminocatalytic enantioselective 1,6 additions of alkyl thiols to cyclic dienones: Vinylogous iminium ion activation
X. Tian, Y. Liu, P. Melchiorre
Angew. Chem. Int. Ed. 2012, 51, 6439-6442