Direct Generation of N‐Alkoxycarbonyl Nitrones from Oximes: Intramolecular Cycloaddition of Oximes Having Alkene Moieties

δ,ϵ‐Unsaturated oximes, on heating with O‐alkyl S‐(pyridin‐2‐yl)carbonothioates (PySCO2R) in refluxing toluene, undergo intramolecular cycloaddition to give N‐alkoxycarbonylated multi‐cyclic compounds. Mechanistic studies indicate that the reaction involves direct generation of N‐alkoxycarbonyl nitr...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2023-11, Vol.365 (22), p.3927-3934
Main Authors: Sagara, Hiroto, Suzuki, Yoshio, Morita, Nobuyoshi, Ban, Shintaro, Tanaka, Kosaku, Yamamoto, Ayaka, Hashimoto, Yoshimitsu, Tamura, Osamu
Format: Article
Language:English
Subjects:
Cyclic compounds
Cycloaddition
DFT calculation
intramolecular cycloaddition
N-alkoxycarbonyl nitorne
O-alkyl S-(pyridin-2-yl)carbonothioates
Oximes
Reagents
Refluxing
Toluene
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Summary:δ,ϵ‐Unsaturated oximes, on heating with O‐alkyl S‐(pyridin‐2‐yl)carbonothioates (PySCO2R) in refluxing toluene, undergo intramolecular cycloaddition to give N‐alkoxycarbonylated multi‐cyclic compounds. Mechanistic studies indicate that the reaction involves direct generation of N‐alkoxycarbonyl nitrones followed by cycloaddition, instead of intramolecular oxime‐olefin cycloaddition (IOOC) followed by alkoxycarbonylation. DFT calculation indicates that N‐alkoxycarbonylation of oxime with PySCO2R is a concerted reaction. The reaction of oxime with a chiral alkoxycarbonylation reagent exhibits a reasonably high diastereo‐face selectivity.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202300793