4.7 Article

Aminocatalyzed Synthesis of Enantioenriched Phenalene Skeletons through a Friedel-Crafts/Cyclization Strategy

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JOURNAL OF ORGANIC CHEMISTRY
卷 83, 期 2, 页码 1019-1025

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AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.7b02629

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  1. University of Versailles-St-Quentin-en-Yvelines

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A series of enantioenriched phenalene-derived compounds were accessed by a Friedel - Crafts/cyclization strategy. Starting from a,alpha,beta-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 properties.

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