Synthesis of highly substituted pyroglutamates via a domino Michael addition–Claisen rearrangement–lactamisation approach

Abstract

Chelated enolates are versatile nucleophiles for Michael additions to α,β-unsaturated allylic esters. By quenching the reaction with TMSCl and heating a subsequent Ireland–Claisen rearrangement can occur. Direct cyclisation of the rearrangement product gives rise to highly substituted pyroglutamic acid derivatives.