The synthesis and reactivity in an [4+2] inverse electron demand hetero Diels-Alder reaction (ihDA )of an original class of electron-poor heterodienes, the N-substituted-1H-benzo[c][1,2]thiazin-4-one-2,2-dioxides, are described. These are highly reactive electro-philes that allow easy access to unprecedented benzo-thiazine glyco-fused derivatives in a remarkably selective way, even when using acetylated glycals, previously unexplored within this version of ihDA. DFT calculations support the experimental data, and moreover show that acetylated dienophiles can easily react making cycloadditions feasible

Benzo[c][1,2]thiazine‐Based Analogs in the Inverse Electron Demand [4+2] Hetero Diels‐Alder Reaction with Glycals: Access to Tetracyclic Fused Galactose and Fucose Derivatives / Biagiotti, Giacomo; Legnani, Laura; Aresta, Giusi; Chiacchio, Maria A.; Richichi, Barbara. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1434-193X. - ELETTRONICO. - 2022:(2022), pp. e202200769.1-e202200769.9. [10.1002/ejoc.202200769]

Benzo[c][1,2]thiazine‐Based Analogs in the Inverse Electron Demand [4+2] Hetero Diels‐Alder Reaction with Glycals: Access to Tetracyclic Fused Galactose and Fucose Derivatives

Biagiotti, Giacomo
Data Curation
;
Aresta, Giusi
Data Curation
;
Richichi, Barbara
Supervision
2022

Abstract

The synthesis and reactivity in an [4+2] inverse electron demand hetero Diels-Alder reaction (ihDA )of an original class of electron-poor heterodienes, the N-substituted-1H-benzo[c][1,2]thiazin-4-one-2,2-dioxides, are described. These are highly reactive electro-philes that allow easy access to unprecedented benzo-thiazine glyco-fused derivatives in a remarkably selective way, even when using acetylated glycals, previously unexplored within this version of ihDA. DFT calculations support the experimental data, and moreover show that acetylated dienophiles can easily react making cycloadditions feasible
2022
1
9
Biagiotti, Giacomo; Legnani, Laura; Aresta, Giusi; Chiacchio, Maria A.; Richichi, Barbara
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/1290287
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