Iridium catalyzed enantioselective hydrogenation of alpha-alkoxy and beta-alkoxy vinyl ethers
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Iridium catalyzed, enantioselective hydrogenations of functionalized, acid-sensitive vinyl ethers are reported. These reactions are mediated by the chiral N-carbene-oxazoline complex 1 that, unlike similar N,P-ligated catalysts (6 and 7), gives hydrogenation products (with enantioselectivities up to 96%) without significant acid-mediated degradation. In general, higher enantioselectivities were observed for the allylic alcohol derivatives (2) than the -methoxycinnamate-based compounds (4). 2012 The Royal Society of Chemistry.