Hypervalent iodine compounds have been used in many useful synthetic transformations on organic molecules.  Furthermore, these reagents tend to be more environmentally benign than heavy metal-containing reagents used to perform similar reactions.  In combination, these attributes make iodine reagents attractive for asymmetric synthesis. Previous work has shown that chiral hypervalent iodine reagents can transfer chirality to their substrates with a moderate level of selectivity.  The best compounds to date place the iodine reagent within a 5- or 6- membered ring containing a heteroatom (O).  However, to date, research regarding the effects of a remote heteroatom on hypervalent iodine stability and reactivity has been limited.  Therefore, two classes of target compounds, 1 & 2, were designed to facilitate further study of this phenomenon.  These compounds place iodine in 6- and 7- membered rings with nitrogen as the stabilizing heteroatom.  Progress toward the synthesis of these compounds is presented.

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