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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Chiral Phosphoric Acid-Catalyzed Asymmetric [4 + 2] Cycloadditions of Photogenerated o-Quinodimethanes with
Shu-Wei Gan1, Yu Zhou2, Yu-Mei Ma1
1Precise Synthesis and Function Development Key Laboratory of Sichuan Province, College of Chemistry and Chemical Engineering, China West Normal University, No. 1 Shida Road, Nanchong 637002, P. R. China.
Abstract:
Chiral cyclohexyl-appended azaarenes are highly sought synthetic targets in biochemistry and medicinal chemistry. Herein we report a chiral phosphoric acid-catalyzed asymmetric [4 + 2] cycloaddition reaction between photogenerated o-quinodimethanes and alkenylazaarenes. A wide range of cyclohexyl-appended azaarenes are obtained in moderate to high yields (up to 85%) with high diastereoselectivities (up to 20:1 dr) and excellent enantioselectivities (up to 98% ee). A scale-up experiment and derivatizations of products demonstrate the practical utility of this synthetic method.
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