A new stereoselective synthesis of trisubstituted alkenes is developed. Hydrophosphoryloxylation of haloalkynes provides Z-alkenyl halophosphates, which undergo Pd-catalyzed consecutive cross-coupling reactions to afford regio- and stereodefined trisubstituted alkenes.

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A Regio-and Stereoselective Synthesis of Trisubstituted Alkenes via Gold(I)-Catalyzed Hydrophosphoryloxylation of Haloalkynes. -A highly stereoselective synthesis of Z-alkenyl halophosphates (III) starting from substituted iodo-and bromoalkynes (I) is achieved using a Au catalyst. The obtained products can easily be functionalized via consecutive Pd-catalyzed cross coupling reactions of the vinyl halide resp. phosphate functionalities to give regio-and stereodefined trisubstituted alkenes such as (VII), (X) and (XIII). -(CHARY, B. C.; KIM*, S.; SHIN, D.; LEE, P. H.; Chem. Commun. (Cambridge) 47 (2011) 27, 7851-7853, http://dx.

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