Nucleophilic properties of a nonstabilized azomethine ylide derived from sarcosine and cyclohexanone. A novel domino reaction leading to substituted 4-aryl-2-pyrrolidones

Abstract

A nonstabilized asymmetric azomethine ylide derived from sarcosine and cyclohexanone reacts with 3-substituted coumarins and ethyl benzylidene malonate to give 4-aryl-2-pyrrolidones in moderate yields, and the adducts of classical 1,3-dipolar cycloadditions as the minor products. The main reaction proceeds via a domino process, starting with 1,4-nucleophilic addition to the conjugated double bond, and represents the first example of the nucleophilic properties of a nonstabilized azomethine ylide. © 2012 Published by Elsevier Ltd.