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(IT) and Ag(I) complexes occurred at gamma-position preferably. Only (E)-isomer was observed in the reactions. This method provides an alternative for the synthesis of gamma-hydroxyl or gamma-amino acid derivatives. (c) 2007 Elsevier Ltd. All rights reserved.