254115-13-4Relevant academic research and scientific papers
An asymmetric aminohydroxylation approach to the azepine core of (-)-balanol
Masse, Craig E.,Morgan, Adam J.,Panek, James S.
, p. 2571 - 2573 (2007/10/03)
(equation presented) An efficient formal synthesis of the potent protein kinase C inhibitor (-)-balanol that relies on a modified asymmetric aminohydroxylation of the α,β-unsaturated aryl ester (1) is reported. The aryl ester functionality and the dihydroquinyl alkaloid ligand system (DHQ)2-AQN are used to control the regio- and enantioselectivity of the process.
Reversal of Regioselection in the Sharpless Asymmetric Aminohydroxylation of Aryl Ester Substrates
Morgan, Adam J.,Masse, Craig E.,Panek, James S.
, p. 1949 - 1952 (2008/02/11)
(Matrix Presented) 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.
