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Deracemization of α-Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals

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Lee,  Ji-Woong
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Lee, J.-W., & List, B. (2012). Deracemization of α-Aryl Hydrocoumarins via Catalytic Asymmetric Protonation of Ketene Dithioacetals. Journal of the American Chemical Society, 134(44), 18245-18248. doi:10.1021/ja3096202.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0010-2504-8
Abstract
An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic α-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Brønsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5)2C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.