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. Issue 43 (14th November 2022)

• Record Type: Journal Article
• Authors: Biagiotti, Giacomo; Legnani, Laura; Aresta, Giusi; Chiacchio, Maria A.; Richichi, Barbara
• Is Part Of: European journal of organic chemistry. Volume 2022:Issue 43(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-11-14
• Subjects: Benzo[c][1, 2]thiazine -- Glycomimetics -- Heterodienes -- Diels-Alder reaction -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202200769
• Languages: English
• ISSNs: 1434-193X

Abstract

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 electrophiles 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. Abstract : The N ‐substituted‐3‐thioxo‐benzo[ c ][1, 2]thiazin‐4‐one‐2, 2‐dioxides are an original class of highly reactive electron‐poor heterodienes that allow easy access to unprecedented benzo‐thiazine bearing galactose and fucose derivatives in a remarkably selective way.