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pubmed-article:16492030pubmed:abstractTextThe 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.lld:pubmed
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pubmed-article:16492030pubmed:dateRevised2011-5-23lld:pubmed
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pubmed-article:16492030pubmed:articleTitlePalladium-catalyzed chemo- and enantioselective oxidation of allylic esters and carbonates.lld:pubmed
pubmed-article:16492030pubmed:affiliationDepartment of Chemistry, Stanford University, California 94305-5080, USA. bmtrost@stanford.edulld:pubmed
pubmed-article:16492030pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:16492030pubmed:publicationTypeResearch Support, N.I.H., Extramurallld:pubmed