Preparation and DFT studies of chiral Cu (I)-complexes of biphenyl bisoxazolines and their application in enantioselective Kharasch–Sosnovsky reaction

Effect of a range of t -butyl perbenzoates bearing electron-withdrawing and electron-donating substitutions on the phenyl ring and HZSM-5 as a porous additive at 0 °C in enantioselective allylic C–H bond oxidation of cyclic and acyclic olefins in the presence of Cu (I)-( S, a S,S ) complexes of biph...

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Bibliographic Details
Published in:Scientific reports 2022-09, Vol.12 (1), p.15038-15038, Article 15038
Main Authors: Samadi, Saadi, Arvinnezhad, Hamid, Mansoori, Sirwan, Parsa, Hadi
Format: Article
Language:English
Subjects:
639/638/403
639/638/403/935
639/638/549/972
639/638/77/883
639/638/77/888
Biphenyl
Chelation
Chemical activity
Copper
Enantiomers
Equilibrium
Esters
Humanities and Social Sciences
Ligands
multidisciplinary
Oxidation
Porous materials
Science
Science (multidisciplinary)
Temperature
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Summary:Effect of a range of t -butyl perbenzoates bearing electron-withdrawing and electron-donating substitutions on the phenyl ring and HZSM-5 as a porous additive at 0 °C in enantioselective allylic C–H bond oxidation of cyclic and acyclic olefins in the presence of Cu (I)-( S, a S,S ) complexes of biphenyl bisoxazoline ligands, produced easily through the chelation-induced process, were investigated. The enantioenriched allylic esters were obtained in reasonable times with excellent enantioselectivities and yields using electron-withdrawing substituted peresters in the presence of Cu (I)-( S, a S,S ) -1a complex, containing phenyl groups at the stereogenic centers of the oxazoline moieties. To reach a better insight on geometry, chemical activity, enantioselectivity, and thermodynamic stability of the Cu (I)-BOX complexes, DFT calculations with B3LYP-D3/6-31G ( d , p ) level of theory were applied to them. Moreover, NBO analysis was used to illustrate interactions between orbitals.
ISSN:2045-2322
2045-2322
DOI:10.1038/s41598-022-18922-1