77481-20-0Relevant academic research and scientific papers
Selective Lewis acid complexation of 2-hydroxyethyl esters using competitive Diels-Alder reactions as a mechanistic probe
Clapham, Gary,Shipman, Michael
, p. 1127 - 1134 (2000)
Competitive Diels-Alder reactions involving ethyl acrylate, 2- hydroxyethyl acrylate and 2-methoxyethyl acrylate indicate that certain Lewis acids (e.g. EtAlCl2) selectively complex to the 2-hydroxyethyl ester group. Studies using ethyl 2-hydroxyethyl fumarate support these findings. 13C NMR spectroscopy provides some evidence regarding the nature of the interactions between 2-hydroxyethyl esters and EtAlCl2. The influence of EtAlCl2 on the level of diastereocontrol observed in the Diels-Alder reactions of (2R*,3R*)-2-(3-hydroxy)butyl acrylate is described. (C) 2000 Elsevier Science Ltd.
