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Reversal of Regioselection in the Sharpless Asymmetric Aminohydroxylation of Aryl Ester Substrates

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journal contribution
posted on 10.11.1999, 00:00 by Adam J. Morgan, Craig E. Masse, James S. Panek
The asymmetric synthesis of β-hydroxy-α-amino acids is reported which relies on the use of α,β-unsaturated aryl ester substrates and the dihydroquinyl alkaloid ligand system (DHQ)2-AQN to control the regio- and enantioselectivity of the asymmetric aminohydroxylation (AA) process. α,β-Unsaturated ester substrates of type 1 have a significant effect on the substrate−ligand recognition event which results in a reversal of regioselectivity in the AA reaction.