N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-[epsi]-Lactones

N-Heterocyclic Carbene Catalyzed [4+3] Annulation of Enals and o-Quinone Methides: Highly Enantioselective Synthesis of Benzo-[epsi]-Lactones

Enantioselectivity through H bonding: An unprecedented [4+3] annulation of enals with o-quinone methides catalyzed by N-heterocyclic carbenes (NHCs) to give benzo-ε-lactones is described. High to excellent enantioselectivity was achieved by using a chiral triazolium NHC having a free OH group, which...

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Veröffentlicht in:Angewandte Chemie International Edition 2013-08, Vol.52 (33), p.8607
Hauptverfasser: Lv, Hui, Jia, Wen-Qiang, Sun, Li-Hui, Ye, Song
Format: Artikel
Sprache:eng
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Zusammenfassung:Enantioselectivity through H bonding: An unprecedented [4+3] annulation of enals with o-quinone methides catalyzed by N-heterocyclic carbenes (NHCs) to give benzo-ε-lactones is described. High to excellent enantioselectivity was achieved by using a chiral triazolium NHC having a free OH group, which participates in a hydrogen-bonding interaction with the substrate.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201303903