Synthesis, Characterization, and Study of Catalytic Activity of Chiral Cu(II) and Ni(II) Salen Complexes in the α-Amino Acid C-α Alkylation Reaction.

Autor: Tovmasyan AS; Scientific and Production Center 'Armbiotechnology' of NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia., Mkrtchyan AF; Scientific and Production Center 'Armbiotechnology' of NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia.; Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia., Khachatryan HN; Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia., Hayrapetyan MV; Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia., Hakobyan RM; Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA, 26 Azatutyan Ave., Yerevan 0014, Armenia., Poghosyan AS; Scientific and Production Center 'Armbiotechnology' of NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia., Tsaturyan AH; Scientific and Production Center 'Armbiotechnology' of NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia.; Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia., Minasyan EV; Scientific and Production Center 'Armbiotechnology' of NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia.; Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia., Maleev VI; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia., Larionov VA; A.N. Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia.; Faculty of Science, Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklaya Str. 6, 117198 Moscow, Russia., Ayvazyan AG; Scientific and Technological Center of Organic and Pharmaceutical Chemistry of NAS RA, 26 Azatutyan Ave., Yerevan 0014, Armenia., Shibata N; Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Showa-ku, Nagoya 466-8555, Japan., Roviello GN; Institute of Biostructures and Bioimaging, Italian National Council for Research (IBB-CNR), Area di Ricerca Site and Headquarters, Via Pietro Castellino 111, 80131 Naples, Italy., Saghyan AS; Scientific and Production Center 'Armbiotechnology' of NAS RA, 14 Gyurjyan Str., Yerevan 0056, Armenia.; Institute of Pharmacy, Yerevan State University, 1 Alex Manoogian Str., Yerevan 0025, Armenia.
Jazyk: angličtina
Zdroj: Molecules (Basel, Switzerland) [Molecules] 2023 Jan 25; Vol. 28 (3). Date of Electronic Publication: 2023 Jan 25.
DOI: 10.3390/molecules28031180
Abstrakt: A new family of Cu(II) and Ni(II) salen complexes was synthesized and fully characterized through various physicochemical methods. Their catalytic activity was evaluated in the phase transfer C α -alkylation reaction of the Schiff bases of D,L-alanine ester and benzaldehyde derivatives. It was found that the introduction of a chlorine atom into the ortho - and para -positions of the phenyl ring of the substrate resulted in an increase in both the chemical yield and the asymmetric induction ( ee 66-98%). The highest enantiomeric excess was achieved in the case of a Cu(II) salen complex based on ( S , S )-cyclohexanediamine and salicylaldehyde at -20 °C. The occurrence of a bulky substituent in the ligand present in the complexes led to a drastic decrease in ee and chemical yield. For instance, the introduction of bulky substituents at positions 3 and 5 of the phenyl ring of the catalyst resulted in a complete loss of the stereoselectivity control in the alkylation reaction.
Databáze: MEDLINE
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