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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 (free Supporting Information)


Abstract

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.

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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