Activation of the dienophilicity of indoles in normal electron demand [4 + 2] cycloadditions under high pressure.
[reaction: see Text] Activation by either high pressure or a combination of Lewis acid catalysis and high pressure allows indole derivatives to behave as dienophiles in [4 + 2] cycloaddition reactions under mild conditions. The biactivation mode has the highest impact on the stereoselectivity of the reaction. The cycloadducts resulting from these reactions are characterized by boat-shape conformations that bear well-defined orthogonal planes.
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Laboratoire des Fonctions Azotées et Oxygénées Complexes, UMR 6014 CNRS, Université de Rouen-IRCOF, Rue Tesnière, F-76821 Mont Saint Aignan, France.
Hess
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Toupet
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Piettre
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