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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Visible-Light-Excited Lewis Acid Catalyzed Intermolecular [2σ + 3π] Photocycloadditions
Tianlei Du1, Yunzhi Xie2, Qiujie Qin1
1College of Sciences, Shanghai University, 99 Shangda Road, Shanghai 200444, P. R. China.
Abstract:
Herein, we introduce an innovative approach employing a direct visible-light-excited Lewis acid-catalyzed [2σ + 3π] cycloaddition reaction between bicyclo[1.1.0]butanes and α-vinyl azides via diradical intermediate. This transformation proceeds efficiently in the absence of any external photocatalyst produces versatile 2-azabicyclo[3.1.1]heptene derivatives with a broad substrate scope, achieving yields of up to 94% across 34 examples. The synthetic practicality was further demonstrated through a scaled-up reaction, and the transformation of the imidazole auxiliary into an ester group.
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