叔丁基（苯磺酰基）烷基-N-羟基氨基甲酸酯：第一类N-（Boc）硝酮等效物。

tert-Butyl (phenylsulfonyl)alkyl-N-hydroxycarbamates: the first class of N-(Boc) nitrone equivalents.

作者信息

Guinchard Xavier, Vallée Yannick, Denis Jean-Noël

机构信息

Laboratoire d'Etudes Dynamiques et Structurales de la Sélectivité, UJF-CNRS, Institut de Chimie Moléculaire de Grenoble, Université Joseph Fourier, Grenoble 1, BP 53, 38041 Grenoble Cedex 9, France.

出版信息

Org Lett. 2005 Nov 10;7(23):5147-50. doi: 10.1021/ol051766c.

DOI:10.1021/ol051766c

PMID:16268524

Abstract

[reaction: see text] tert-Butyl (phenylsulfonyl)alkyl-N-hydroxycarbamates 1 have been easily prepared from aldehydes and tert-butyl N-hydroxycarbamate in a methanol-water mixture using sodium benzenesulfinate and formic acid. These sulfones 1 behave as N-(Boc)-protected nitrones 4 in the reaction with organometallics to give N-(Boc)hydroxylamines. Some chemical transformations showing their interest as building blocks in organic synthesis are described.

摘要

[反应：见正文] 叔丁基（苯磺酰基）烷基-N-羟基氨基甲酸酯1已通过使用苯亚磺酸钠和甲酸，由醛和叔丁基N-羟基氨基甲酸酯在甲醇-水混合物中轻松制备。这些砜1在与有机金属化合物反应生成N-（Boc）-羟胺时表现为N-（Boc）保护的硝酮4。描述了一些表明它们作为有机合成中构建单元具有价值的化学转化。