Cycloaddition Reactions of Sugar-Based Olefins, Nitrones and Nitrile Oxides: En Route to Saccharidic Spiroisoxazoli(di)nes

摘要: Isoxazoline- and isoxazolidine-containing compounds are privileged structures of interest, notably in synthetic medicinal chemistry. These heterocycles can be obtained by 1,3-dipolar cycloaddition reactions between an olefin a nitrile oxide or nitrone. This reaction generates one C–C C–O bond up to three chiral centres step. In the present chapter, we aim summarize discuss reports these cycloadditions on sugar olefins, with focus exo-methylene sugars activated exo-glycals, leading saccharidic spiroisoxazoli(di)nes high regio- stereocontrol. Additional examples involving nitrone, oxide, nitrone two partners will also discussed. Due importance spiro structure several biologically active compounds, spiroheterocycles regarded as spironucleoside analogues, mimics natural building blocks multicyclic scaffolds suitable for selective derivatization. Some them thus showed promising biological properties antibacterial agents enzyme inhibitors. Moreover, labile nature N–O isoxazolidine ring makes it attractive target chemists. The reactivity this scaffold has therefore been widely studied, cycloadducts have converted other classes interest. Examples relevance use spiro-sugars given chapter.