Designing N-Heterocyclic Carbenes: Simultaneous Enhancement of Reactivity and Enantioselectivity in the Asymmetric Hydroacylation of Cyclopropenes

Faster, higher, stronger! The N‐heterocyclic carbene (NHC) catalyzed diastereo‐ and enantioselective hydroacylation of cyclopropenes affords structurally valuable acylcyclopropanes. A new family of electron‐rich, 2,6‐dimethoxyphenyl‐substituted NHCs induces excellent reactivity and enantioselectivit...

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Veröffentlicht in:	Angewandte Chemie International Edition 2011-12, Vol.50 (52), p.12626-12630
Hauptverfasser:	Liu, Fan, Bugaut, Xavier, Schedler, Michael, Fröhlich, Roland, Glorius, Frank
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation Asymmetry Carbenes Catalysis Catalysts Chemical Sciences Crystallography, X-Ray Cyclopropanes - chemical synthesis Cyclopropanes - chemistry cyclopropenes enantioselective catalysis Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry hydroacylation Methane - analogs & derivatives Methane - chemical synthesis Methane - chemistry Models, Molecular Molecular Structure N-heterocyclic carbenes Organic chemistry Organic compounds organocatalysis Reaction kinetics Stereoisomerism Transformations
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Beschreibung
Zusammenfassung:	Faster, higher, stronger! The N‐heterocyclic carbene (NHC) catalyzed diastereo‐ and enantioselective hydroacylation of cyclopropenes affords structurally valuable acylcyclopropanes. A new family of electron‐rich, 2,6‐dimethoxyphenyl‐substituted NHCs induces excellent reactivity and enantioselectivity. Preliminary kinetic studies unambiguously demonstrated the superiority of this family of catalysts over known NHCs in this challenging transformation.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201106155