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

Autor:	Marco Leusciatti, Mattia Moiola, Paolo Quadrelli, Marco Corti, Mariella Mella
Rok vydání:	2020
Předmět:	Nitrile Tertiary amine 010405 organic chemistry Organic Chemistry Halide Carbohydrate 010402 general chemistry 01 natural sciences Catalysis 0104 chemical sciences Adduct chemistry.chemical_compound chemistry Diels alder Organic chemistry Organic synthesis Ene reaction
Zdroj:	Synthesis. 53:574-586
ISSN:	1437-210X 0039-7881
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7dd5741999ad9e2a635cef674407c5d3 https://doi.org/10.1055/s-0040-1707276 Zobrazit plný text záznamu