155130-53-3Relevant academic research and scientific papers
A Chelation-Controlled Ester Enolate Claisen Rearrangement
Krafft, Marie E.,Dasse, Olivier A.,Jarrett, Sandra,Fievre, Anne
, p. 5093 - 5101 (2007/10/02)
The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state.An oxygen-bearing functional group at the tetriary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. α,β-Disubstituted unsaturated carboxylic acids are also formed with high diastereoselectivity.
A ligand assisted Claisen rearrangement
Krafft, Marie E.,Jarrett, Sandra,Dasse, Olivier A.
, p. 8209 - 8212 (2007/10/02)
The Ireland ester enolate Claisen rearrangement gives rise to Z-trisubstituted alkenes via heteroatom mediated substrate pre-organization prior to rearrangement.
