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Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions
- Huang, Xiaoqiang, Quinn, Taylor R., Harms, Klaus, Webster, Richard D., Zhang, Lilu, Wiest, Olaf, Meggers, Eric
- Journal of the American Chemical Society 2017 v.139 no.27 pp. 9120-9123
- Lewis acids, catalytic activity, cycloaddition reactions, rhodium
- A reaction design is reported in which a substrate-bound chiral Lewis acid complex absorbs visible light and generates an excited state that directly reacts with a cosubstrate in a highly stereocontrolled fashion. Specifically, a chiral rhodium complex catalyzes visible-light-activated intermolecular [2+2] cycloadditions, providing a wide range of cyclobutanes with up to >99% ee and up to >20:1 d.r. Noteworthy is the ability to create vicinal all-carbon-quaternary stereocenters including spiro centers in an intermolecular fashion.