Copper-catalyzed allylic hydroxyamination and amination of alkenes with Boc-hydroxylamine

Article abstract of DOI:10.1016/j.tetlet.2005.01.024

Olefins react regioselectively with Boc-NHOH in the presence of Cu(I,II) salts to produce allyl-N(OH)(Boc) derivatives, apparently via the intermediacy of Boc-NO; yields and rates are dramatically improved by the addition of H ₂O₂. The corresponding allylamine derivatives, allyl-NH(Boc), are formed selectively from Boc-NHOH/olefin with CuBr/P(OEt) ₃.