Synthesis of beta-amino-alpha-hydroxy esters and beta-amino-alpha-azido ester by Sharpless asymmetric aminohydroxylation, byproducts analysis.
[reaction: see text] Synthesis of enantiomerically pure beta-amino-alpha-hydroxy esters (1, 2) and beta-amino-alpha-azido ester (3) using Sharpless AA as a key step is described. A hitherto unreported side reaction, the oxidation of the beta-hydroxy-alpha-amino ester (5) into the alpha,alpha-di-tert-butyloxycarbamoyl-beta-ketoester (8) under AA conditions, is documented.
Liu
Zuosheng
Z
Institut de Chimie des Substances Naturelles, CNRS, 91198 Gif-sur-Yvette Cedex, France.
Ma
Nianchun
N
Jia
Yanxing
Y
Bois-Choussy
Michèle
M
Malabarba
Adriano
A
Zhu
Jieping
J