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

Tert-Butyl (phenylsulfonyl)alkyl-N-hydroxycarbamates 1 have been easily prepared from aldehydes and tert-butyl N-hydroxycarbamate in a 41 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.