Intramolecular, Visible-Light-Mediated Aza Paternò-Büchi Reactions of Unactivated Alkenes
Dominique E. Blackmun, Stephen Chamness, Corinna S. Schindler
Abstract
Azetidines are of particular interest in medicinal chemistry for their favorable properties, including increased resistance to oxidative metabolism and lower lipophilicity. The recent development of [2 + 2] reactions has significantly expanded the limited repertoire of methods for azetidine synthesis, but access to more complex architectures still requires further development. Herein, we report a visible-light-enabled intramolecular [2 + 2] cycloaddition of unactivated alkenes that proved previously unreactive to access tricyclic azetidines with 3D complex structures and high levels of saturation.
Topics & Concepts
ChemistryAzetidineIntramolecular forceLipophilicityCycloadditionCombinatorial chemistryStereochemistryOrganic chemistryCatalysisSynthesis and Catalytic ReactionsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions