Corrigendum to “Enantioselective synthesis of homocarbocyclic-2′-oxa-3′-azanucleosides”

Chiacchio, Ugo; Saita, Maria Grazia; Crispino, Lia; Gumina, Giuseppe; Mangiafico, Sebastiano; Pistarà, Venerando; Romeo, Giovanni; Piperno, Anna; Clercq, Erik De

doi:10.1016/j.tet.2007.03.013

Tetrahedron

2007

DOI: 10.1016/j.tet.2007.03.013

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Corrigendum to “Enantioselective synthesis of homocarbocyclic-2′-oxa-3′-azanucleosides”

Ugo Chiacchio

Maria Grazia Saita

Lia Crispino

et al.

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

Sagara,

Suzuki,

Morita

et al. 2023

Adv Synth Catal

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δ,ε‐Unsaturated oximes, on heating with O‐alkyl S‐(pyridin‐2‐yl)carbonothioates (PySCO<sub>2</sub>R) 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 PySCO<sub>2</sub>R is a concerted reaction. The reaction of oxime with a chiral alkoxycarbonylation reagent exhibits a reasonably high diastereo‐face selectivity.

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

Sagara,

Suzuki,

Morita

et al. 2023

Adv Synth Catal

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BF₃-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes

et al. 2015

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A C-amide-substituted O-silylated oxime, (E)-(tert-butyldimethylsiloxyimino)acetic acid N,N-dimethylamide (8b), on treatment with 2.2 equiv of BF3·OEt2, in situ generated boracyclic nitrone-type intermediate BF3·14, which underwent cycloaddition with alkenes to give 3,5-cis-isoxazolidines as the major products. The mechanism was strongly supported by isolation of the reaction intermediate 14 that was characterized by X-ray diffraction and its further reaction. This cycloaddition was successfully applied to the synthesis of syn-HPA-12 known as an inhibitor of CERT that mediates the transport of ceramide.

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Corrigendum to “Enantioselective synthesis of homocarbocyclic-2′-oxa-3′-azanucleosides”

Cited by 2 publications

References 0 publications

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

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

BF₃-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes

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Corrigendum to “Enantioselective synthesis of homocarbocyclic-2′-oxa-3′-azanucleosides”

Cited by 2 publications

References 0 publications

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

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

BF3-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes

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Product

Resources

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BF₃-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes