Diversity-oriented synthesis of N,N,O-trisubstituted hydroxylamines from alcohols and amines by N—O bond formation

A method for producing a trisubstituted hydroxylamine, the method comprising reacting a monoperoxyacetal compound with a secondary amide, wherein the monoperoxyacetal compound has the structure I or II

• wherein
• R1 is a substituted or unsubstituted linear or branched alkyl group, a substituted or unsubstituted cycloalkyl group or heterocycloalkyl group, a polyether group, an alkylpolyether group, or a protected or unprotected monosaccharide, disaccharide, or polysaccharide, and
• R2 is hydrogen, an aryl group, a heteroaryl group, or a substituted or unsubstituted alkyl group;
• and
• the secondary amide has the structure IV
• wherein
• R5 and R6 are, independently, a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group or heterocycloalkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or wherein R5 and R6 together form a substituted or unsubstituted cycloalkyl group or heterocycloalkyl group, and
• M+is Li, MgBr, MgCI, or Mgl, wherein the secondary amide is produced by reacting a secondary amine with a Grignard reagent or an alkyl lithium, and
• wherein the trisubstituted hydroxylamine has the structure V
• wherein a molar ratio of monoperoxyacetal compound to the secondary amide is from 1:1 to 1:5.