Synthesis of highly substituted pyroglutamates via a domino Michael addition-Claisen rearrangement-lactamisation approach.
Chelated enolates are versatile nucleophiles for Michael additions to alpha,beta-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.
Schmidt
Christian
C
Institut für Organische Chemie, Universität des Saarlandes, D-66123 Saarbrücken, Germany.
Kazmaier
Uli
U
D003500:Cyclization; D007769:Lactams / Q000737:chemistry*; D011761:Pyrrolidonecarboxylic Acid / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007769:Lactams; D011761:Pyrrolidonecarboxylic Acid