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Synfacts 2008(8): 0868-0868
DOI: 10.1055/s-2008-1078513
DOI: 10.1055/s-2008-1078513
Metal-Mediated Synthesis
© Georg Thieme Verlag
Stuttgart ˙ New York
Stereocomplementary Preparation and Coupling of β-Keto Ester Enol Tosylates
H. Nakatsuji, K. Ueno, T. Misaki, Y. Tanabe*
Kwansei Gakuin University, Sanda, Japan
Further Information
Publication History
Publication Date:
23 July 2008 (online)
Significance
The conversion of β-keto esters into enol sulfonates and the subsequent cross-coupling is a useful method for the preparation of substituted acrylates. This is the first practical method of the stereoselective synthesis of enol sulfonates from readily available keto esters. Both (Z)- and (E)-sulfonates can be easily obtained by this route with more than 95:5 selectivity. The same reagent (TsCl-NMI-Et3N) is also very useful for the preparation of sterically hindered secondary alkyl tosylates.