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

Submitting author affiliation:
Lomonosov Moscow State University, Moscow, Russian Federation

Beilstein Arch. 2022, 202240. https://doi.org/10.3762/bxiv.2022.40.v1

Published 31 May 2022

Preprint

Abstract

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.

Keywords: cathodic cyclopropane opening; stereoselective electrosynthesis; voltammetric testing; amino acids, cysteine derivatives; Ni Schiff-base complexes

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Levitskiy, O. A.; Aglamazova, O. I.; Grishin, Y. K.; Magdesieva, T. V. Beilstein Arch. 2022, 202240. doi:10.3762/bxiv.2022.40.v1

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