Tethered aza-Wacker cyclizations allow for the syntheses of a variety of heterocycles that are known to have important applications. We have developed a novel method for the diastereoselective construction of cyclic phosphoramidates using tethered aza-Wacker chemistry. We identified that a phosphoramidate tether with an unusual 5-chloro-8-quinolinol “arm” was essential for achieving &gt;20:1 diastereoselectivity in these reactions, presumably through palladium chelation. The substrate scope with respect to alkenyl alcohols and the phosphoramidate tether was extensively explored. This cyclization reaction scaled well, and the product phosphoramidate heterocycles were valuable synthons, including for tether removal. From chiral alkenyl precursors, highly diastereoselective cyclization reactions furnished enantiopure cyclic phosphoramidate products.

Highly regio- and diastereoselective tethered aza-Wacker cyclizations of alkenyl phosphoramidates

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