Stereoselective Synthesis of Acetoacetate-Derived Enol Triflates
2008; American Chemical Society; Volume: 10; Issue: 13 Linguagem: Inglês
10.1021/ol8010002
ISSN1523-7060
AutoresDavid J. Babinski, Omid Soltani, Doug E. Frantz,
Tópico(s)Asymmetric Synthesis and Catalysis
ResumoA 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.
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