Whilst the use of chiral cations in asymmetric catalysis is well established, the use of chiral anions has received little attention until relatively recently.1 This presentation will discuss the application of the concept of chiral anion phase-transfer catalysis to the enantioselective fluorinative dearomatization of phenols.2 Our process employs chiral phosphoric acid catalysts to take simple and readily available phenols and transform them efficiently and with high enantioselectivity into fluorinated chiral small molecules bearing reactive functionality under ambient reaction conditions. The close relationship of the products with well-studied ortho-quinols provides numerous avenues for synthetic elaboration as well as exciting opportunities for bioisosteric replacement of hydroxyl with fluorine in natural products.1. For a review: Phipps, R. J.; Hamilton, G. L.; Toste, F. D. Nature Chem. 2012 , 4, 603 2. Phipps, R. J.; Toste, F. D. J. Am. Chem. Soc. 2013 , 135, 1268.

Chiral anion phase-transfer catalysis applied to the direct enantioselective fluorinative dearomatization of phenols

246th National Meeting (2013)

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