Preparation of stereodefined enol tosylates and their use in cross-coupling reactions

ORGN 682

Dietrich Steinhuebel, Shane Krska, Jenny Baxter, Michael Palucki, and Ian W. Davies. Department of Process Research, Merck & Co, Rahway, NJ 07065
The preparation of stereodefined E or Z enol tosylates is presented along with their use in cross-coupling reactions. A variety of trisubstituted unsaturated esters were prepared in moderate to excellent yield via Suzuki-Miyaura and Sonogashira coupling. In addition, the asymmetric hydrogenation of these derivatives will also be presented.