(2+2) Cycloadditions of Methylene exo ‐Glycals: Synthesis of Glycopyranosylidene‐Spiro‐Azetidine‐2‐ones (β‐Lactams) and Cyclobutanones

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Abstract: [2+2] Cycloadditions of methylene exo‐glycal derivatives with chlorosulfonyl isocyanate and dichloroketene were studied in detail, investigating the effect of the carbohydrate moiety, protecting groups as well as reaction temperature on the yields of the transformations. These reactions gave new anomeric spiro‐β‐lactam and spiro‐cyclobutanone derivatives, whose structure was established by 1D and 2D NMR and MS experiments. The transformation of spiro‐cyclobutanone into spiro‐γ‐lactone was also demonstrated.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: (2+2) Cycloadditions of Methylene exo ‐Glycals: Synthesis of Glycopyranosylidene‐Spiro‐Azetidine‐2‐ones (β‐Lactams) and Cyclobutanones ; day:23 ; month:02 ; year:2023 ; extent:11
European journal of organic chemistry ; (23.02.2023) (gesamt 11)

Creator: József, János
Somsák, László
Tóth, Marietta
Juhász, László

DOI: 10.1002/ejoc.202201488

URN: urn:nbn:de:101:1-2023022414025584432644

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 14.08.2025, 10:58 AM CEST

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József, János
Somsák, László
Tóth, Marietta
Juhász, László

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(2+2) Cycloadditions of Methylene exo ‐Glycals: Synthesis of Glycopyranosylidene‐Spiro‐Azetidine‐2‐ones (β‐Lactams) and Cyclobutanones

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Other Objects (12)

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Cooperative Chiral Lewis Base/Palladium‐Catalyzed Asymmetric Syntheses of Methylene‐Containing δ‐Lactams

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