| Institution: | 1. Department of Chemistry, Federal University of São Carlos—UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil;2. Department of Chemistry, Federal University of São Carlos—UFSCar, Centre of Excellence for Research in Sustainable Chemistry, (CERSusChem), São Carlos, São Paulo, Brazil
Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany;3. Institut für Organische Chemie, Universität Regensburg, Universitätsstrasse 31, 93053 Regensburg, Germany |
| 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 tetrahydrocyclobutac]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. |
