Bifunctional Ammonium Salt Catalyzed Asymmetric α-Hydroxylation of β-Ketoesters by Simultaneous Resolution of Oxaziridines.

Johanna NovacekJoseph A IzzoMathew J VetticattMario Waser

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2016)

Chiral bifunctional urea-containing ammonium salts were found to be very efficient catalysts for asymmetric α-hydroxylation reactions of β-ketoesters with oxaziridines under base-free conditions. The reaction is accompanied by a simultaneous kinetic resolution of the oxaziridine and a plausible and so far unprecedented bifunctional transition-state model has been obtained by means of DFT calculations.

Keyphrases

highly efficient
ionic liquid
metal organic framework
density functional theory
room temperature
single molecule
molecular dynamics
solid state
molecular docking
molecular dynamics simulations
monte carlo