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. 1999 Dec 16;1(12):1949-52.
doi: 10.1021/ol9903032.

Reversal of regioselection in the sharpless asymmetric aminohydroxylation of aryl ester substrates

A J Morgan  1 , C E Masse, J S Panek
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Reversal of regioselection in the sharpless asymmetric aminohydroxylation of aryl ester substrates

A J Morgan et al. Org Lett. .

Abstract

[formula: see text] The asymmetric synthesis of beta-hydroxy-alpha-amino acids is reported which relies on the use of alpha,beta-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. alpha,beta-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.

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