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Enantioenriched fluorinated heterocycles can be prepared through fluorocyclizations of prochiral indoles (see scheme; Ts=tosyl, Bn=benzyl, Boc=tert-butoxycarbonyl). More than twenty examples for this cascade fluorination-cyclization, which is catalyzed by cinchona alkaloids and employs N-fluorobenzenesulfonimide as the electrophilic fluorine source have been explored, and an unprecedented catalytic asymmetric difluorocyclization has also been identified.

Original publication

DOI

10.1002/anie.201103151

Type

Journal article

Journal

Angew Chem Int Ed Engl

Publication Date

22/08/2011

Volume

50

Pages

8105 - 8109