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Issue 7, 2012
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A computational study of the origin of stereoinduction in NHC-catalyzed annulation reactions of α,β-unsaturated acyl azoliums

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Abstract

The origin of stereoselectivity of NHC-catalyzed annulation reactions of ynals and stable enols was studied with Density Functional Theory. The data suggest that the C–C bond formation is the stereo-determining step. Only the deprotonated pathway (containing an oxy-anion and overall neutral species) was found to give rise to discrimination of the competing stereoisomers. This is due predominantly to electrostatic repulsion of the β-stabilizing enolate functionality with the π-cloud of the aryl group in the NHC-catalyst.

Graphical abstract: A computational study of the origin of stereoinduction in NHC-catalyzed annulation reactions of α,β-unsaturated acyl azoliums

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Publication details

The article was received on 15 Mar 2012, accepted on 22 Apr 2012 and first published on 24 Apr 2012


Article type: Edge Article
DOI: 10.1039/C2SC20331F
Citation: Chem. Sci., 2012,3, 2346-2350

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    A computational study of the origin of stereoinduction in NHC-catalyzed annulation reactions of α,β-unsaturated acyl azoliums

    E. Lyngvi, J. W. Bode and F. Schoenebeck, Chem. Sci., 2012, 3, 2346
    DOI: 10.1039/C2SC20331F

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