Aminocatalyzed Synthesis of Enantioenriched Phenalene Skeletons through a Friedel–Crafts/Cyclization Strategy
| Autor: | Vincent Coeffard, Xavier Moreau, Maxime Giardinetti, Christine Greck, Jérôme Marrot |
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| Přispěvatelé: | Institut Lavoisier de Versailles (ILV), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Centre National de la Recherche Scientifique (CNRS), Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation (CEISAM), Université de Nantes - Faculté des Sciences et des Techniques, Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS), Université de Versailles Saint-Quentin-en-Yvelines (UVSQ)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Nantes - UFR des Sciences et des Techniques (UN UFR ST), Université de Nantes (UN)-Université de Nantes (UN)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC) |
| Rok vydání: | 2018 |
| Předmět: | |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, 2018, 83 (2), pp.1019-1025. ⟨10.1021/acs.joc.7b02629⟩ Journal of Organic Chemistry, American Chemical Society, 2018, 83 (2), pp.1019-1025. ⟨10.1021/acs.joc.7b02629⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.7b02629 |
| Popis: | International audience; 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. |
| Databáze: | OpenAIRE |
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