Regioselectivity in Lewis acids catalyzed X–H (O, S, N) insertions of methyl styryldiazoacetate with benzyl alcohol, benzyl thiol, and aniline

Different from Rh(II) catalysts, X–H (X = O, S, N) insertion of methyl styryldiazoacetate catalyzed by Lewis acids including Cu(I), Cu(II) and Ag(I) complexes occurred at γ-position preferably. Only (E)-isomer was observed in the reactions. This method provides an alternative for the synthesis of γ-hydroxyl or γ-amino acid derivatives.