Regio- and stereoselective 1,2-addition to alkenes resulting in the incorporation of two different vicinal functional groups is a highly sought synthetic manipulation. Here in we wish to report our results from a systematic exploration of the co-addition of I-Nu across the double bonds using in situ generated acyl-hypoiodite intermediates 78 and 80 (not shown here) obtained from the oxidation of elemental iodine with hypervalent iodine reagents, 44 and 65 respectively, a variety of nucleophiles can be used, often as cosolvents in the reaction or tethered nucleophiles in the substrate as in 102 to obtain the highly functionalized products shown in the box. [Graphic]
