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 |
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Format: | Artikel |
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. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/anie.201405381 |