A fully-telescoped, aqueous, auxiliary-mediated asymmetric transformation

Abstract

Dedicated to Professor Eusebio AbstractA fully-telescoped, aqueous, auxiliary-mediated Diels-Alder cycloaddition in moderate selectivity is reported. The auxiliary is prepared from L-asparagine and trimethylacetaldehyde, and coupled without isolation to the acryloyl substrate. Direct addition of cyclopentadiene generates the cycloadduct, which is cleaved from the heterocycle upon mild treatment with acid and heat. A significantly reduced selectivity is observed relative to the two-pot synthesis in which the acrylamide is precipitated and washed prior to the cycloaddition. Vacuum-assisted removal of the acrylic acid contaminant prior to the cycloaddition substantially remedies the reduced selectivities achieved in the one-pot transformation relative to the two-step sequence. Four chemical transformations, not including acid/base reactions, are accomplished in this onepot synthesis.

Studying Reactivity Relationships of Copolymers N-naphthylacrylamide with (Acrylicacid and Methylacrylate)

“…Monomers of N-substituted acryl amide were prepared by a reaction of acryloyl chloride with different amines (1,2). Many of these monomers were copolymerized and terpolymerized with other monomers (3,4), several of these copolymers were used as drugs and pigments (5,6).…”