The generation and trapping of two new nitrosocarbonyl intermediates bearing carbohydrate-based
chiral substituents is achieved by the mild oxidation of the corresponding nitrile
oxides with tertiary amine N-oxides. Their capture with suitable dienes and alkenes afforded the corresponding
hetero Diels–Alder cycloadducts and ene adducts from fair to excellent yields. The
entire methodology looks highly promising by the easy conversion of aldoximes into
hydroxymoyl halides, widening the access to nitrosocarbonyls, versatile tools in organic
synthesis.
Key words
nitrosocarbonyl - hetero Diels–Alder reactions - ene reactions - nitrile oxides -
synthetic applications
