A Chelation-Controlled Ester Enolate Claisen Rearrangement

…, OA Dasse, S Jarrett, A Fievre

文献索引：Krafft, Marie E.; Dasse, Olivier A.; Jarrett, Sandra; Fievre, Anne Journal of Organic Chemistry, 1995 , vol. 60, # 16 p. 5093 - 5101

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被引用次数: 16

摘要

The Ireland ester enolate Claisen rearrangement gives rise to 2-trisubstituted alkenes due to heteroatom-enforced control over the conformation of the transition state. An oxygen-bearing functional group at the tertiary carbinol center, which can coordinate to the enolate metal via a seven-membered chelated transition state, provides the control element to explain the selectivity. a $-Disubstituted unsaturated carboxylic acids are also formed with high ...