Stereoselective synthesis of acetoacetate-derived enol triflates.
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.
Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.
David
D
Babinski
Omid
O
Soltani
Doug E
DE
Frantz
D000090:Acetoacetates / Q000737:chemistry*; D008698:Mesylates / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000090:Acetoacetates; D008698:Mesylates; C016635:acetoacetic acid