Photocatalyzed Intramolecular [2+2] Cycloaddition of <i>N</i>‐Alkyl‐<i>N‐(</i>2‐(1‐arylvinyl)aryl)cinnamamides
Wanderson C. de Souza, Bianca T. Matsuo, Priscilla Mendonça Matos, José Tiago Menezes Correia, Marília S. Santos, Burkhard König, Márcio W. Paixão
Abstract
N-Alkyl-N-(2-(1-arylvinyl)aryl)cinnamamides are converted into natural product inspired scaffolds via iridium photocatalyzed intramolecular [2+2] photocycloaddition. The protocol has a broad substrate scope, whilst operating under mild reaction conditions. Tethering four components forming a trisubstituted cyclobutane core builds rapidly high molecular complexity. Our approach allows the design and synthesis of a variety of tetrahydrocyclobuta[c]quinolin-3(1H)-ones, in yields ranging between 20-99 %, and with excellent regio- and diastereoselectivity. Moreover, it was demonstrated that the intramolecular [2+2]-cycloaddition of 1,7-enynes-after fragmentation of the cyclobutane ring-leads to enyne-metathesis-like products.