Jump to main content
Jump to site search

Issue 24, 2008
Previous Article Next Article

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

Author affiliations

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.

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

Back to tab navigation

Publication details

The article was received on 04 Jul 2008, accepted on 20 Aug 2008 and first published on 28 Oct 2008


Article type: Paper
DOI: 10.1039/B811382C
Citation: Org. Biomol. Chem., 2008,6, 4643-4648
  •   Request permissions

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

    C. Schmidt and U. Kazmaier, Org. Biomol. Chem., 2008, 6, 4643
    DOI: 10.1039/B811382C

Search articles by author

Spotlight

Advertisements