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Stereoselective Enol Tosylation: Preparation of Trisubstituted α,β-Unsaturated Esters

Jenny M. Baxter,* Dietrich Steinhuebel, Michael Palucki, and Ian W. Davies

*Department of Process Research, Merck & Co., Inc., P.O. Box 2000, Rahway, New Jersey 07065, Email:

J. Baxter, D. Steinhuebel, M. Palucki, I. W. Davies, Org. Lett., 2005, 7, 215-218.

DOI: 10.1021/ol047854z

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(E)- or (Z)-trisubstituted α,β-unsaturated esters have been prepared in three steps from N-protected glycine. The key step is the highly selective enol tosylation of γ-amino β-keto esters followed by an effective Suzuki-Miyaura coupling reaction with a variety of aryl boronic acids.

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Key Words

Enol Tosylation, Sulfonates, Suzuki Coupling, Alkenylation

ID: J54-Y2005-100