Stereoselective Synthesis of Acetoacetate-Derived Enol Triflates
- 10 June 2008
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (13), 2901-2904
- https://doi.org/10.1021/ol8010002
Abstract
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)(4)NOH ( E-selective) in combination with triflic anhydride to provide a practical and predictable approach to these valuable substrates.Keywords
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