Hydroxylamines and sulfinamide as amine components in the Petasis boronic acid–Mannich reaction: synthesis of N-hydroxy or alkoxy-α-aminocarboxylicacids and N-(tert-butyl sulfinyl)-α-amino carboxylicacids

An efficient synthesis of N-hydroxy or alkoxy-α-aminocarboxylic acids and N-(tert-butyl sulfinyl)-α-amino carboxylic acids has been developed from N,O-alkyl or hydroxylamines and tert-butyl sulfinamide utilizing a Petasis boronic acid–Mannich reaction. The scope and limitations of this method have been examined.