Catalytic asymmetric intermolecular stetter reaction of heterocyclic aldehydes with nitroalkenes: backbone
Daniel A DiRocco1, Kevin M Oberg, Derek M Dalton
1Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523, USA.
Abstract:
The catalytic asymmetric intermolecular Stetter reaction of heterocyclic aldehydes and nitroalkenes has been developed. We have identified a strong stereoelectronic effect on catalyst structure when a fluorine substituent is placed in the backbone. X-ray structure analysis provides evidence that hyperconjugative effects are responsible for a change in conformation in the azolium precatalyst. This new N-heterocyclic carbene precursor bearing fluorine substitution in the backbone results in significantly improved enantioselectivities across a range of substrates.
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