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  • Title: Palladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates.
    Author: Trost BM, Richardson J, Yong K.
    Journal: J Am Chem Soc; 2006 Mar 01; 128(8):2540-1. PubMed ID: 16492030.
    Abstract:
    The palladium-catalyzed oxidation of allylic esters and carbonates using a novel potassium nitronate has been developed. This method is highly chemoselective, leaving other esters, alcohols, thioethers, and amines undisturbed. The oxidation can be operated in two modes: an achiral mode, using either PPh3 or rac-2 as ligand, or a chiral and highly enantioselective mode, using 2 as ligand. The oxidative enantioselective desymmetrization of meso bis-esters provides a significantly shorter method to arrive at commonly used synthetic intermediates compared to other strategies. Highly efficient kinetic resolution is also possible using this methodology.
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