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

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Nitrosocarbonyl Carbohydrate Derivatives: Hetero Diels–Alder and Ene Reaction Products for Useful Organic Synthesis
Synthesis ( IF 2.2 ) Pub Date : 2020-09-22 , DOI: 10.1055/s-0040-1707276
Paolo Quadrelli _{1,

1} , Marco Corti , Marco Leusciatti , Mattia Moiola , Mariella Mella

Affiliation

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.

Publication History

Received: 06 July 2020

Accepted after revision: 08 August 2020

Publication Date:
22 September 2020 (online)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

中文翻译：

亚硝基羰基碳水化合物衍生物：有用的有机合成的杂Diels–Alder和Ene反应产物

摘要

两种新的带有碳水化合物基手性取代基的亚硝基羰基中间体的生成和捕获是通过相应的腈氧化物与叔胺N-氧化物的轻度氧化来实现的。用合适的二烯和烯烃捕获后，相应的杂Diels-Alder环加合物和烯加合物的收率从中等到优异。整个方法学看起来很有希望，因为醛肟易于转化为羟酰卤化物，拓宽了有机合成中广泛使用的亚硝基羰基化合物的使用范围。