Selective complexation of 2-hydroxyethyl esters using Lewis acids

Article abstract of DOI:10.1016/S0040-4039(99)01051-5

Competitive Diels-Alder reactions between ethyl acrylate and 2- hydroxyethyl acrylate (1,3-cyclopantadiene, CH₂Cl₂, 0°C) in the presence of a variety of Lewis acids indicate that selective complexation of the 2- hydroxyethyl ester can be accomplished, most notably using EtAlCl₂. Further Diels-Alder reactions using ethyl 2-hydroxyethyl fumarate support these findings. ¹³C NMR studies provide direct evidence for the nature of the interactions between 2-hydroxyethyl esters and EtAlCl₂.