Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 44, Pages 18245-18248Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja3096202
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Funding
- Max Planck Society
- European Research Council
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An unprecedented catalytic asymmetric protonation of ketene dithioacetals is described. Various racemic alpha-aryl hydrocoumarin derivatives are transformed into enantioenriched dithioacetal-protected hydrocoumarins in the presence of a chiral Bronsted acid catalyst. A newly developed phosphoric acid, featuring the 3,5-bis(pentafluorothio)phenyl (3,5-(SF5)(2)C6H3) substituent, is introduced. The obtained products can be easily converted into either hydrocoumarins or the corresponding chromans via simple hydrolysis or hydrogenation, respectively.
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