Highly Asymmetric NHC-Catalyzed Hydroacylation of Unactivated Alkenes

Highly Asymmetric NHC-Catalyzed Hydroacylation of Unactivated Alkenes

NHC‐catalysis proto(n)type: The title reaction produces 21 different chroman‐4‐one‐type products in good yields and excellent enantioselectivities, in each case building up a new all‐carbon quaternary stereocenter (see scheme). Based on DFT calculations a mechanistic scenario involving proton transf...

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Veröffentlicht in:Angewandte Chemie International Edition 2011-05, Vol.50 (21), p.4983-4987
Hauptverfasser: Piel, Isabel, Steinmetz, Marc, Hirano, Keiichi, Fröhlich, Roland, Grimme, Stefan, Glorius, Frank
Format: Artikel
Sprache:eng
Schlagworte:
enantioselective catalysis
hydroacylation
N-heterocyclic carbenes
organocatalysis
Stetter reaction
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Zusammenfassung:NHC‐catalysis proto(n)type: The title reaction produces 21 different chroman‐4‐one‐type products in good yields and excellent enantioselectivities, in each case building up a new all‐carbon quaternary stereocenter (see scheme). Based on DFT calculations a mechanistic scenario involving proton transfer, possible transition states, and a mode of enantioinduction is presented.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201008081