Direct
Visible-Light-Excited Asymmetric Lewis Acid
Catalysis of Intermolecular [2+2] Photocycloadditions

Meggers, Eric

Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions

Version 2 2018-06-23, 13:13

Version 1 2017-06-28, 20:45

Posted on 2018-06-23 - 13:13

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.

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Huang, Xiaoqiang; Quinn, Taylor R.; Harms, Klaus; Webster, Richard D.; Zhang, Lilu; Wiest, Olaf; et al. (2017). Direct Visible-Light-Excited Asymmetric Lewis Acid Catalysis of Intermolecular [2+2] Photocycloadditions. ACS Publications. Collection. https://doi.org/10.1021/jacs.7b04363

https://doi.org/10.1021/jacs.7b04363

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