We thank the European Union (PIEF-GA-2009-235510 to T.M., PIEF-GA-2008-220034 to O.L.), GSK (G.B.) and the Berrow Foundation for a scholarship to G.T.G. We also thank Dr. S. Fletcher for very helpful discussions.
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Communication
Organocatalyzed Enantioselective Fluorocyclizations†
Article first published online: 12 JUL 2011
DOI: 10.1002/anie.201103151
Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Lozano, O., Blessley, G., Martinez del Campo, T., Thompson, A. L., Giuffredi, G. T., Bettati, M., Walker, M., Borman, R. and Gouverneur, V. (2011), Organocatalyzed Enantioselective Fluorocyclizations. Angew. Chem. Int. Ed., 50: 8105–8109. doi: 10.1002/anie.201103151
- †
Publication History
- Issue published online: 17 AUG 2011
- Article first published online: 12 JUL 2011
- Manuscript Received: 8 MAY 2011
Funded by
- European Union. Grant Numbers: PIEF-GA-2009-235510, PIEF-GA-2008-220034
- GSK
Keywords:
- alkaloids;
- asymmetric catalysis;
- fluorocyclizations;
- indoles;
- organocatalysis
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.