β-Amino Esters via the Reformatsky Reaction: Restraining Effects of the ortho-Methoxyphenyl Substituent.

Abstract β-Amino esters are, in most cases, the only products of the Reformatsky reaction in CH 2 Cl 2 between (methoxycarbonyl)methyl zinc bromide (prepared in-situ ) and imines prepared from either an aryl or alkyl aldehyde and o -anisdine (Scheme 2). Restraining properties of the ortho -methoxyphenyl group, which lead to sole formation of the β-amino ester, are ascribed to the inductive effect of the ortho -methoxy substituent.