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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Intramolecular, Visible-Light-Mediated Aza Paternò-Büchi Reactions of Unactivated Alkenes
Dominique E Blackmun1, Stephen A Chamness1, Corinna S Schindler1
1Department of Chemistry, Willard-Henry-Dow Laboratory, University of Michigan, 930 N University Ave., Ann Arbor, Michigan 48109, United States.
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.
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