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Asymetryczne reakcje pericykliczne katalizowane kompleksami magnezu

Czombik Anna

Wiadomości Chemiczne

2022

[Z] 76, 9-10

755--788

II Group-metals, like magnesium, are one of the most widespread elements in the environment. The abundance of II-group metals in the Earth’s crust is over 108 times greater than the precious metals. For the industrial applications, the important factors are the low costs of production and higher accessibility of their compounds. This puts the spotlight on alkaline-earth metals competing with transition elements as catalysts in organic synthesis. Features of their derivatives, like mild Lewis acidity and strong Brønsted basicity enabled them to catalyze reactions where Lewis-acidactivation of the substrate is essential. In this review the emphasis was put on magnesium-catalyzed pericyclic reactions, which are recognized as one of the most important methods of new carbon-carbon or carbon-heteroatom bonds formation. Using the catalysts based on II-group metal cations and chiral ligands, a highly stereoselective conversion of achiral substrates into enantioenriched products is possible. The Mg-based catalysts have been used in Diels-Alder, ene and 1,3-dipolar additions. Described synthesis methods were characterized by high efficiency (chemical yields and enantiomeric excesses). Where applicable, the relationships between the structure of catalyst/substrates, conditions and efficiency were discussed. Just now there are a few applications, for example in synthesis of alkaloid (–)-manzacidine or antibiotic of algal origin – (–)-malyngolide.