Aminocatalyzed Synthesis of Enantioenriched Phenalene Skeletons through a Friedel-Crafts/Cyclization Strategy
Maxime Giardinetti1, Jérôme Marrot1, Christine Greck1
1Institut Lavoisier de Versailles, UMR CNRS 8180, Université de Versailles-St-Quentin-en-Yvelines , 45 Avenue des États-Unis, Versailles 78035 Cedex, France.
Abstract:
A series of enantioenriched phenalene-derived compounds were accessed by a Friedel-Crafts/cyclization strategy. Starting from α,β-unsaturated aldehydes and 2-naphthol derivatives, high levels of enantioselectivity were obtained through iminium-enamine catalysis. The catalytic system composed of a diphenylprolinol silyl ether organocatalyst and triethylamine as a base was applied to a combination of diversely functionalized substrates. The obtained phenalene-derived architectures are promising building blocks for reaching natural products and exhibit fluorescence properties.
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