Stereoselectivity of nitrile oxide cycloadditions to chiral allylic fluorides: experiment and theory.
The cycloadditions of nitrile oxides with new and previously studied allylic fluorides were examined. The 1,3-dipolar cycloaddition reactions were also investigated theoretically with density functional theory (B3LYP) based transition-state modelling. The predictions provided reasonable agreement with experiment, indicating that both steric and electronic effects have important influences on the stereoselectivities of these reactions.
Prakesch
Michael
M
ENSCR, Laboratoire de Synthèses et Activations de Biomolécules CNRS UMR 6052, Avenue de Général Leclerc, 35 700 Rennes Beaulieu, France.
Grée
Danielle
D
Grée
René
R
Carter
Jennifer
J
Washington
Ilyas
I
Houk
K N
KN
D005459:Fluorides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D009570:Nitriles; D010087:Oxides; D005459:Fluorides