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Highly Regio- and Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates
preprintsubmitted on 28.02.2021, 16:44 and posted on 03.03.2021, 04:58 by Anand H. Shinde, Annu Thomas, Joel T Mague, Shyam Sathyamoorthi
We present highly diastereoselective tethered
aza-Wacker cyclization reactions of alkenyl phosphoramidates. “Arming” the phosphoramidate tether with 5-chloro-8-quinolinol was essential to achieving >20:1 diastereoselectivity in these reactions. The substrate scope with respect to alkenyl alcohols and phosphoramidate tether was extensively explored. The scalability of the oxidative cyclization was demonstrated, and the product cyclophosphoramidates were shown to be valuable synthons, including for tether removal. With chiral alkenyl precursors, enantiopure cyclic phosphoramidates were formed.