Journal of Organic Chemistry p. 5093 - 5101 (1995)
Update date:2022-07-29
Topics:
Krafft, Marie E.
Dasse, Olivier A.
Jarrett, Sandra
Fievre, Anne
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.
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