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Synfacts 2011(4): 0438-0438  
DOI: 10.1055/s-0030-1259616
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric α-Fluorination of Cyclic Ketones

Contributor(s): Benjamin List, Anna Lee
P. Kwiatkowski, T. D. Beeson, J. C. Conrad, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
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Publication History

Publication Date:
18 March 2011 (online)

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Significance

MacMillan and co-workers report a highly efficient asymmetric α-fluorination of cyclic ketones using cinchona amine catalyst D. This process allows general access to a variety of α-fluorinated carbo- and heterocyclic ketones with high yields and enantioselectivities. Furthermore, their enamine activation protocol was shown to be regio- and diastereoselective in the α-fluorination of complex substrates, such as the steroid cholestanone.