Selective Synthesis of 3-Substituted Pyrrolidinones by Enol-Passerini and Anomalous Enol-Passerini Condensations

Org Lett. 2018 Jul 6;20(13):3875-3878. doi: 10.1021/acs.orglett.8b01462. Epub 2018 Jun 26.

Abstract

Enols are used for the first time in a condensation with aldehydes and isocyanides to selectively give three- or pseudo-four-component adducts, depending on the reaction conditions. These new transformations have proven to be a convenient alternative for the synthesis of biologically relevant pyrrolidinones containing peptidic or pseudo-peptidic groups on carbon 3. More importantly, this work attests to the utility of heterocyclic enols containing conjugated electron-withdrawing groups as useful reagents in isocyanide-based multicomponent reactions.

Publication types

  • Research Support, Non-U.S. Gov't