Corey‐Сhaykovsky cyclopropanation of dehydroalanine in the Ni(II) coordination environment: Electrochemical vs. chemical activation

Levitskiy, Oleg A.; Aglamazova, Olga I.; Grishin, Yu. K.; Нефедов, С. Е.; Magdesieva, Tatiana V.

doi:10.1016/j.electacta.2022.139980

Cited by 9 publications

(10 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…: +374 60 710 410. 11 . However, the main questions that accompany new methods for the development of non-protein amino acids synthesis, to wit, availability of starting substances, high chemical and asymmetric yields, exclusion of racemization remain urgent and unsolved.…”

Section: Asymmetric Synthesis Of Derivatives Of Alanine Via Michael A...mentioning

confidence: 99%

Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study

Mkrtchyan

Tovmasyan²,

Paloyan³

et al. 2022

Synlett

View full text Add to dashboard Cite

Ni(II) complex of the Schiff base of the chiral auxiliary (S)-2-N-(N'-benzylprolyl)aminobenzophenone (BPB) and dehydroalanine as the initial complex in the addition reaction was investigated. The obtained four new derivatives of -alanine were investigated as inhibitors of aldose reductase. Only one of them: (S)-2-amino-3-((4-methylbenzyl)amino)propanoic acid showed activity. It becomes a reason for studying the patterns of biological activity of the structure of -amino acids. The results of docking analysis indicated that (S)-2-amino-3-((4-methylbenzyl)amino)propanoic acid demonstrated the ability to form bonds with different functional groups of the enzyme which let us assume that some amino acids of non-functional groups, such as Trp20 of ALR2, can play a key role in inhibitor-enzyme interactions.

show abstract

Section: Asymmetric Synthesis Of Derivatives Of Alanine Via Michael A...mentioning

confidence: 99%

Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study

Mkrtchyan

Tovmasyan²,

Paloyan³

et al. 2022

Synlett

View full text Add to dashboard Cite

show abstract

“…As models, a series of Ni(II)-Schiff base complexes containing α,α-cyclopropanated amino acids was synthesized (see Figure 1). Complexes 1-3 containing an unsubstituted cyclopropane ring (1) or bearing Me (2) and COOMe (3) groups were obtained using previously reported protocols [15,19]. Complex 4 is new.…”

Section: Voltammetry Studymentioning

confidence: 99%

“…Recently, we elaborated a versatile electrochemical approach for the stereoselective functionalization of a side chain of amino acids involved in the Ni(II) chiral coordination environment [9][10][11][12][13][14][15]. A combination of redox-activity and chirality provided by the Ni-Schiff base template, supported with the protection from redox-destruction of the amino acid skeleton, makes the suggested approach a convenient route to various types of nonproteinogenic amino acids [9,10,12,13].…”

Section: Introductionmentioning

confidence: 99%

“…A combination of redox-activity and chirality provided by the Ni-Schiff base template, supported with the protection from redox-destruction of the amino acid skeleton, makes the suggested approach a convenient route to various types of nonproteinogenic amino acids [9,10,12,13]. Recently, several practical approaches to α,α-cyclopropanated amino acids in the form of Ni(II)-Schiff base complexes were suggested [16][17][18][19], including electrochemical ones [15]. Cyclopropanecontaining amino acids are important components of various pharmaceuticals [20,21] and bio-additives [22].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

Levitskiy¹,

Aglamazova²,

Grishin³

et al. 2022

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

The involvement of an α,α-cyclopropanated amino acid in the chiral Ni(II) coordination environment in the form of a Schiff base is considered as a route to electrochemical broadening of the donor–acceptor cyclopropane concept in combination with chirality induction in the targeted products. A tendency to the reductive ring-opening and the follow-up reaction paths of thus formed radical anions influenced by substituents in the cyclopropane ring are discussed. Optimization of the reaction conditions opens a route to the non-proteinogenic amino acid derivatives containing an α–β or β–γ double C=C bond in the side chain; the regioselectivity can be tuned by the addition of Lewis acids. One-pot combination of the reductive ring opening and subsequent addition of thiols allows obtaining the cysteine derivatives in practical yields and with high stereoselectivity at the removed β-stereocenter.

show abstract

“…1). Complexes 1-3 containing unsubstituted cyclopropane ring (1) or bearing Me (2) and COOMe (3) groups were obtained using previously reported protocols [15,19]. Complex (4) is new.…”

Section: Voltammetry Studymentioning

confidence: 99%

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

Levitskiy¹,

Aglamazova²,

Grishin³

et al. 2022

Preprint

View full text Add to dashboard Cite

Involvement of an α,α-cyclopropanated amino acid in the chiral Ni(II) coordination environment in the form of a Schiff-base is considered as a route to electrochemical broadening of the DA-cyclopropane concept in combination with chirality induction in the targeted products. A tendency to the reductive ring-opening and the follow-up reaction paths of thus formed radical-anions influenced by substituents in the cyclopropane ring are discussed. Optimization of the reaction conditions opens a route to the non-proteinogenic amino acid derivatives containing the α-β or β-γ double C=C bond in the side chain; the regioselectivity can be tuned by Lewis acids addition. One-pot combination of the reductive ring opening and subsequent addition of thiols allows obtaining the cysteine derivatives in practical yields and with high stereoselectivity at the removed β-stereocenter.

show abstract

Corey‐Сhaykovsky cyclopropanation of dehydroalanine in the Ni(II) coordination environment: Electrochemical vs. chemical activation

Cited by 9 publications

References 51 publications

Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study

Asymmetric Synthesis of Derivatives of Alanine via Michael Addition Reaction and their Biological Study

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives

Contact Info

Product

Resources

About