tert-Butyl (phenylsulfonyl)alkyl-N-hydroxycarbamates: the first class of N-(Boc) nitrone equivalents.
[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.
Guinchard
Xavier
X
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.
Vallée
Yannick
Y
Denis
Jean-Noël
JN