TY - JOUR A1 - Levitskiy, Oleg A. A1 - Aglamazova, Olga I. A1 - Grishin, Yuri K. A1 - Magdesieva, Tatiana V. T1 - Reductive opening of a cyclopropane ring in the Ni(II) coordination environment: a route to functionalized dehydroalanine and cysteine derivatives JF - Beilstein Archives Y1 - 2022/// SN - M3 - doi:10.3762/bxiv.2022.40.v1 N2 - 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. ER -