Brönsted Acid Catalyzed Multicomponent Synthesis of Phosphorus and Fluorine-Derived γ-Lactam Derivatives

J Org Chem. 2020 Nov 20;85(22):14369-14383. doi: 10.1021/acs.joc.0c00280. Epub 2020 Apr 28.

Abstract

A Brönsted acid multicomponent reaction between pyruvate derivatives, amines, and aldehydes for the preparation of phosphorus and fluorine substituted γ-lactam derivatives is presented. Depending on the substitution in the resulting 1,5-dihydro-2H-pyrrol-2-one substrates, the reaction provides enol- or enamine-derived γ-lactams. Some enantioselective examples of this reaction are also reported using chiral phosphoric acids as organocatalysts. Moreover, several synthetic applications of γ-lactam derivatives are presented including some examples of highly diastereoselective transformations.

Publication types

  • Research Support, Non-U.S. Gov't