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Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2022, Volume: 2022, Number: 3, Article number : e202101435, Pages count : DOI: 10.1002/ejoc.202101435
Authors Kovalevsky Ruslan A. 1,2 , Smirnov Maxim V. 1,2 , Kucherenko Alexander S. 1 , Bykova Kseniya A. 1 , Shikina Elizaveta V. 1,3 , Zlotin Sergei G. 1
Affiliations
1 I.N.Nazarov Laboratory of Fine Organic Synthesis t, N.D. Zelinsky Institute of Organic Chemistry, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
2 Department of Chemistry M.V. Lomonosov Moscow State University Leninskie gory 1–3 119234 Moscow Russian Federation
3 Faculty of Material sciences M.V. Lomonosov Moscow State University Leninskie gory 1–3 119234 Moscow Russian Federation

Abstract: 2-Nitroallylic carbonates were first applied as promising bis-electrophilic C3 synthons for bifunctional squaramide catalyzed asymmetric domino reaction with kojic acid derivatives to afford so far inaccessible nitro compounds bearing two hydroxypyranone units. The reaction products undergo non-catalytic epimerization at the carbon atom next to the nitro group. Plausible mechanism of the epimerization based on reversible formation of intermediate aci-nitro compound is proposed. The double addition products were transformed to configurationally stable acetates and to chiral nitro glutarates, promising precursors to chiral amino glutaric acid derivatives.
Cite: Kovalevsky R.A. , Smirnov M.V. , Kucherenko A.S. , Bykova K.A. , Shikina E.V. , Zlotin S.G.
Organocatalytic Asymmetric Double Addition of Kojic Acids to 2‐Nitroallylic Carbonates
European Journal of Organic Chemistry. 2022. V.2022. N3. e202101435 . DOI: 10.1002/ejoc.202101435 WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:000844513300007
Scopus: 2-s2.0-85123707577
OpenAlex: W4206936006
Citing:
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OpenAlex 6
Scopus 5
Web of science 7
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