Palladium-catalyzed asymmetric allylic amination of a vinylethylene carbonate with N-heteroaromatics

Abstract

Highly enantioselective allylation of a vinylethylene carbonate by asymmetric palladium catalysis has been developed for a variety of N-heteroaromatic substrates. The employed procedure allows for the efficient synthesis of various acyclic nucleoside analogs in good yields (up to 96%) and with high enantioselectivities (up to 99%) at the Pd catalyst amount of 0.5 mol%. In addition, these acyclic nucleosides are demonstrated to undergo rapid transformation to a variety of interesting structurally diverse chiral acyclic nucleosides and isonucleosides.