Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels-Alder and Ene Reaction Products for Useful Organic Synthesis

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.

Automated summary

By mild oxidation of nitrile oxides with tertiary amine N-oxides, two new nitrosocarbonyl intermediates with carbohydrate-based chiral substituents were successfully synthesized and trapped, leading to hetero Diels-Alder cycloadducts and ene adducts from fair to excellent yields. The methodology shows promise in widening access to nitrosocarbonyls, versatile tools in organic synthesis, through easy conversion of aldoximes into hydroxymoyl halides.