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Sequential Visible-Light Photoactivation and Palladium Catalysis Enabling Enantioselective [4+2] Cycloadditions

Miao-Miao Li, Yi Wei, Jie Liu, Hong-Wei Chen, Liang-Qiu Lu* and Wen-Jing Xiao

*College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, People's Republic of China, Email: luliangqiumail.ccnu.edu.cn

M.-M. Li, Y. Wei, J. Liu, H.-W. Chen, L.-Q. Lu, W.-J. Xiao, J. Am. Chem. Soc., 2017, 139, 14707-14713.

DOI: 10.1021/jacs.7b08064 (free Supporting Information)


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Abstract

In an asymmetric [4+2] cycloaddition of vinyl benzoxazinanones with a variety of ketene intermediates via sequential visible-light photoactivation and palladium catalysis, the traceless and transient generation of ketenes from α-diazoketones through visible-light-induced Wolff rearrangement is important for the success of the palladium catalysis.

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proposed mechanism



Key Words

dihydroquinolinones, Wolff rearrangement


ID: J48-Y2017