Synthesis and Characterization of New Compounds by Enzymatically Catalysed Diels-Alder Reactions

Abstract

The Diels-Alder (DA) reaction is one of the important chemical transformations to create the C–C bonds with predicted regio- and stereo-selectivity, which lead to the forming of bulk organic molecules. Despite of the significant efforts in this filed, the control of the stereoselectivity of DA reactions remain so difficult. Despite the significant efforts in this field, controlling of stereoselectivity of DA reactions remains so difficult. The design of the enzymatic DA reactions provides scientists with a huge advantage in increasing the selectivity of DA reaction products. This work aims to apply the friendly environmental method includes the application of the current approach in enzymatic DA reactions by formation the new organic compounds through the enzymatic DA reactions between anthracene derivatives as dines and pyrrole derivatives as dienophiles. All DA reactions were curried out in the inert environment using the nitrogen gas. The prepared compounds were caramelized using various techniques including mass spectroscopy, nuclear magnetic resonance, and Fourier transform infrared. The results showed that all products of DA reactions containing unnatural dienes with endo-configuration, in addition to obtain 53%–94% isolated yields. Consequently, this study provides an efficient method to control the stereochemistry of DA reactions.