CATALYTIC MULTI-COMPONENT COUPLING REACTIONS OF SILYL GLYOXYLATES

Described is the development of catalytic, stereoselective reactions of silyl glyoxylates utilizing Rh(I)-catalyzed additions of aryl boronic acids. This reactivity was translated asymmetrically via additional effort from our laboratory resulting in the development of a novel tricyclo-[2.2.1.0]- ligand which provided levels of enantioinduction previously unseen within these types of systems. The value of this methodology was expanded towards three-component couplings with aryl aldehydes functioning as an electrophilic trap. Investigative efforts were also applied to improving reaction diastereoselectivity through the application of more sterically encumbered glyoxylates.