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Abstract
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Allylic oxidation of alkenes to produce allylic alcohols and allylic esters is one of the most important reactions in organic chemistry. In this reaction, because of the specific nature of the allylic C-H bond, a new functional group is created without the involvement of the double bond. The stereochemistry of this reaction can be controlled by the use of asymmetric methods. Among these methods, providing a chiral environment especially by using chiral catalysts, has attracted much attention because they can use in small amounts and produce enantioenriched compounds. The Betti reaction produces racemic and non-racemic aminobenzylnaphthol ligands. Non-racemic aminobenzylnaphthols can be used as chiral ligands or chiral auxiliaries in asymmetric synthesis. In this work, first, racemic Betti bases were synthesized by the multicomponent reaction of 2-naphthol, benzaldehyde, and ammonium acetate. Then, the resulting enantiomers were separated by the diastereomeric crystallization method using (L)- tartaric acid in ethanol and methanol. Finally, the synthesized chiral Betti bases were used as chiral ligands in allylic oxidation of olefins for the first time and the resulting products were obtained in high yields and moderate enantioselectivities.
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