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

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journal contribution
posted on 20.01.2005, 00:00 by Jenny M. Baxter, Dietrich Steinhuebel, Michael Palucki, Ian W. Davies
The stereoselective preparation of (E)- or (Z)-trisubstituted α,β-unsaturated esters in three steps from N-protected glycine is presented. The key step in the synthesis is the highly selective enol tosylation of γ-amino β-keto esters. The enol tosylates are stable, crystalline compounds that undergo smooth and effective Suzuki−Miyaura coupling reaction with a variety of aryl boronic acids.