Stereoselective synthesis of acetoacetate-derived enol triflates

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Abstract

(Chemical Equation Presented) A highly stereoselective method for preparing (Z)- and (E)-enol triflates derived from substituted acetoacetate derivatives is described. The salient feature of this methodology is the use of Schotten-Baumann-type conditions to control enolate geometry using either aqueous LiOH (Z-selective) or aqueous (Me)4NOH (E-selective) in combination with triflic anhydride to provide a practical and predictable approach to these valuable substrates.

Original languageEnglish
Pages (from-to)2901-2904
Number of pages4
JournalOrganic Letters
Volume10
Issue number13
DOIs
StatePublished - 2008

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