Email this article Electrochemical Stereoselective Cyclopropanation and Ring Opening: a Route to Novel Cysteine Derivatives
- Authors: Levitskiy O.A.1, Magdesieva T.V.1
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Affiliations:
- Lomonosov Moscow State University
- Issue: Vol 122, No 2 (2024): THEMED SECTION: FUNDAMENTAL PRINCIPLES OF ORGANIC ELECTROCHEMISTRY, CREATION OF NEW FUNCTIONAL MATERIALS AND MATERIALS FOR MEDICINE
- Pages: 30-39
- Section: THEMED SECTION: FUNDAMENTAL SCIENTIFIC RESEARCH IN THE FIELD OF NATURAL SCIENCES
- URL: https://journal-vniispk.ru/1605-8070/article/view/303410
- DOI: https://doi.org/10.22204/2410-4639-2024-122-02-30-39
- ID: 303410
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Abstract
A novel strategy for the stereoselective synthesis of cysteine derivatives containing a malonate fragment in the β-position has been proposed, based on a series of consecutive transformations in the Ni(II) Schiff-base coordination environment. Electrochemical Corey–Chaykovsky cyclopropanation of the dehydroalanine complexes followed by reductive ring opening and subsequent Michael addition of S-nucleophiles to thus formed unsaturated amino acids derivatives open a route to novel cysteine derivatives. New protocol for isolation of the substituted aryl cysteines with strong CH acidity via disassembling of the Schiff-base template has been elaborated.
About the authors
Oleg A. Levitskiy
Lomonosov Moscow State University
Author for correspondence.
Email: oal@org.chem.msu.ru
Russian Federation, 1-3 Leninskie Gory, Moscow, 119991, Russia
Tatiana V. Magdesieva
Lomonosov Moscow State University
Email: tvm@org.chem.msu.ru
Professor
Russian Federation, 1-3 Leninskie Gory, Moscow, 119991, RussiaReferences
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