Stereoselective enol tosylation: Preparation of trisubstituted alpha, beta-unsaturated esters

ORGN 769

Jenny M. Baxter, Dietrich Steinhuebel, Michael Palucki, and Ian W. Davies. Process Research, Merck & Co., Inc, PO Box 2000, Rahway, NJ 07065

 


The stereoselective preparation of E or Z trisubstituted a,b-unsaturated esters in three steps from N-protected glycine is presented.  The key step in the synthesis is the highly selective enol tosylation of g-amino b-keto esters.  The enol tosylates are stable, crystalline compounds which undergo smooth and effective Suzuki-Miyaura coupling reaction with a variety of aryl boronic acids.