Reversal of regioselection in the sharpless asymmetric aminohydroxylation of aryl ester substrates.
[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.
Morgan
A J
AJ
Department of Chemistry, Metcalf Center for Science and Engineering, Boston University, Massachusetts 02215, USA.
Masse
C E
CE
Panek
J S
JS
D000111:Acetylcysteine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000596:Amino Acids / Q000138:chemical synthesis*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D007769:Lactams; D008024:Ligands; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D007769:Lactams; D008024:Ligands; C067713:lactacystin; D000111:Acetylcysteine