ChemInform Abstract: Enediolates and Dienediolates of Carboxylic Acids in Synthesis. Synthesis of β,γ-Epoxyacids from α-Chloroketones.

✍ Scribed by E. M. BRUN; S. GIL; R. MESTRES; M. PARRA; F. VILLAR

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 40 KB
• Volume: 29
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199822081

✦ Synopsis

Enediolates and Dienediolates of Carboxylic Acids in Synthesis. Synthesis of β,γ-Epoxyacids from α-Chloroketones. -Lithium dienolates of saturated acids (I) and (XII) react with α-chloroketones to produce highly substituted β,γ-epoxyacids as the major products in most cases. Unsaturated acids such as (XV) yield under similar conditions mixtures of β,γ-epoxyacids and β-lactams. Only bulky ketones such as (V) give a γ-position attack to the epoxide [cf. (XVIII)] that rearranges in part to the highly conjugated system [cf. (XIX)]. -(BRUN, E. M.;