In a convenient and efficient procedure for the solvent-free synthesis of β-hydroxy esters and β-amino esters, various aldehydes and aldimines undergo a Reformatskyreaction mediated by non-activated indium at room temperature to give the corresponding esters in good to excellent yields.
β-Amino esters via the Reformatsky reaction: Restraining effects of the ortho-methoxyphenyl substituent
作者:James C. Adrian、Julia L. Barkin、Lamyaa Hassib
DOI:10.1016/s0040-4039(99)00248-8
日期:1999.3
β-Amino esters are, in most cases, the only products of the Reformatskyreaction in CH2Cl2 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