Stereoselectivity of nitrile oxide cycloadditions to chiral allylic fluorides: experiment and theory |
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| Authors: | Prakesch Michael Grée Danielle Grée René Carter Jennifer Washington Ilyas Houk K N |
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| Institution: | ENSCR, Laboratoire de Synthèses et Activations de Biomolécules CNRS UMR 6052, Avenue de Général Leclerc, 35 700 Rennes Beaulieu, France. |
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| Abstract: | 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. |
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| Keywords: | cycloaddition density functional calculations diastereoselectivity regioselectivity |
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