Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 38, Pages 10232-10236Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201405381
Keywords
asymmetric synthesis; enals; N-heterocyclic carbenes; organocatalysis; spiro-heterocycles
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Funding
- Alexander von Humboldt Foundation
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft [SPP 1179]
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A highly enantioselective N-heterocyclic carbene (NHC) catalyzed formal [3+2] annulation of alpha, beta-unsaturated aldehydes with azaaurones or aurone generating spiro-heterocycles has been developed. The protocol represents a unique NHC-activation-based approach to access spiro-heterocyclic derivatives bearing a quaternary stereogenic center with high optical purity (up to 95% ee).
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