2024 : 4 : 29
Saadi Samadi

Saadi Samadi

Academic rank: Associate Professor
ORCID:
Education: PhD.
ScopusId: 36017420200
Faculty: Faculty of Science
Address: Department of Chemistry, Faculty of Science, University of Kurdistan, Zip Code 66177-15175, Sanandaj, Iran.
Phone: 4264

Research

Title
Synthesis of chiral (R)- and (S)-Betti bases and investigation the copper complexes of them in asymmetric allylic oxidation of olefins
Type
Presentation
Keywords
Chiral Betti base, R-(+)-1,1′-bi-2-naphthol, Diastereomeric recrystallization, Chiral allylic ester
Year
2023
Researchers Sara Hoseini ، Shiva Majidian ، Arezu Ghaderi ، Saadi Samadi

Abstract

Betti bases are pharmaceutically and synthetically important scaffolds that are readily synthesized through a Mannich-type three-component condensation, known as the Betti reaction, from β-naphthol, aldehyde, and 1° or 2° amine. The most important application of chiral betti bases is their application in asymmetric synthesis, either as chiral ligands or chiral auxiliaries. The Kharasch-Sosnovsky reaction, which involves the copper-catalyzed allylic oxidation of olefins with peresters, is a highly effective method for performing direct C-H bond functionalization at the allylic position of olefins. The asymmetric Kharasch–Sosnovsky reaction of cyclic olefins has been developed with high enantioselectivities. Racemic aminonaphthol 1-(α-N-piperidylbenzyl)-2-naphthol is obtained from simple condensation of benzaldehyde, 2-naphthol and piperidine in ethanol under refluxing conditions. The racemic aminonaphthol has been resolved by diastereomeric recrystallization method using R-(+)-1,1′-bi-2-naphthol and boric acid. Subsequently, the copper complexes of these chiral ligands were investigated for asymmetric allylic C-H bond oxidation of olefins, resulting in high yields of chiral allylic esters with moderate enantioselectivity .