Journal
CHEMICAL SCIENCE
Volume 3, Issue 7, Pages 2346-2350Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c2sc20331f
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Funding
- Swiss National Science Foundation
- ETH Zurich
- NIH [GM-079339]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R01GM079339] Funding Source: NIH RePORTER
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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 beta-stabilizing enolate functionality with the pi-cloud of the aryl group in the NHC-catalyst.
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