N-Heterocyclic Carbene Catalyzed Formal [3+2] Annulation Reaction of Enals: An Efficient Enantioselective Access to Spiro-Heterocycles

A highly enantioselective N‐heterocyclic carbene (NHC) catalyzed formal [3+2] annulation of α,β‐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 be...

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Veröffentlicht in:Angewandte Chemie International Edition 2014-09, Vol.53 (38), p.10232-10236
Hauptverfasser: Guo, Chang, Schedler, Michael, Daniliuc, Constantin G., Glorius, Frank
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Sprache:eng
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Zusammenfassung:A highly enantioselective N‐heterocyclic carbene (NHC) catalyzed formal [3+2] annulation of α,β‐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). Ring, ring: A highly enantioselective formal [3+2] annulation of α,β‐unsaturated aldehydes with azaaurones or aurone is catalyzed by an N‐heterocyclic carbene (NHC) and generates spiro‐heterocycles. The protocol represents a unique NHC activation‐based approach to access spiro‐heterocyclic derivatives bearing a quaternary stereogenic center with high optical purity.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201405381