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Stereoselective Synthesis of Acetoacetate-Derived Enol Triflates

David Babinski, Omid Soltani and Doug E. Frantz*

*Department of Biochemistry, University of Texas Southwestern Medical Center at Dallas, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, Email: doug.frantzutsa.ed

D. Babinski, I. Soltani, D. E. Frantz, Org. Lett., 2008, 10, 2901-2904.

DOI: 10.1021/ol8010002


Highly stereoselective methods for preparing enol triflates derived from substituted acetoacetate derivatives under Schotten-Baumann-type conditions provide either Z enolate geometry using aqueous LiOH or E using aqueous (Me)4NOH in combination with triflic anhydride.

see article for more examples

Practical Synthesis of Aryl Triflates under Aqueous Conditions

D. E. Frantz, D. G. Weaver, J. P. Carey, M. H. Kress, U. H. Dolling, Org. Lett., 2002, 4, 4717-4718.

Key Words

Sulfonates, Schotten-Baumann conditions

ID: J54-Y2008-1870