We have recently discovered a catalytic asymmetric method for the preparation of homo-allylic amines directly from aldehydes over a broad range of aromatic, alkenyl and achiral aliphatic substrates.The successful catalyst system results from the synergistic interplay between the chiral polyboroxinate Br�nsted acid and nonchiral benzoic acid. The mode of synergetic catalysis and the origin of enantioselection observed in this reaction are investigated using a combination of experimental kinetic isotope effects (KIEs), NMR spectroscopy (11B and 13C) and theoretical calculations. The results from these mechanistic studies provide fine details of the enantioselectivity determining transition state geometry.

Origin of enantioselectivity in direct catalytic asymmetric aminoallylation of aldehydes: Synergistic interplay of chiral and nonchiral BrØnsted acids

244th National Meeting (2012)

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