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Highly Enantioselective Hetero-Diels–Alder Reaction of 1,3-Bis-(silyloxy)-1,3-dienes with Aldehydes Catalyzed by Chiral Disulfonimide

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Guin,  Joyram
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Rabalakos,  Constantinos
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List,  Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Citation

Guin, J., Rabalakos, C., & List, B. (2012). Highly Enantioselective Hetero-Diels–Alder Reaction of 1,3-Bis-(silyloxy)-1,3-dienes with Aldehydes Catalyzed by Chiral Disulfonimide. Angewandte Chemie International Edition, 51(35), 8859-8863. doi:10.1002/anie.201204262.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0010-3A43-D
Abstract
Bulking up with F: The title reaction proceeds using 1 mol % of the new perfluoroisopropyl chiral disulfonimide catalyst 1 to deliver several 2,6-disubstituted and 2,5,6-trisubstituted dihydropyrones in good yields and with excellent enantiomeric ratios. The utility of this methodology is illustrated with the first enantioselective synthesis of a potent aromatase inhibitor.