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

Abstract

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

Publikationsverlauf

Eingereicht: 06. Juli 2020

Angenommen nach Revision: 08. August 2020

Artikel online veröffentlicht:
22. September 2020

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