Abstract

Competitive Diels–Alder reactions involving ethyl acrylate, 2-hydroxyethyl acrylate and 2-methoxyethyl acrylate indicate that certain Lewis acids (e.g. EtAlCl 2) 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 EtAlCl 2. The influence of EtAlCl 2 on the level of diastereocontrol observed in the Diels–Alder reactions of (2 R ∗,3 R ∗)-2-(3-hydroxy)butyl acrylate is described.

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