Chemoenzymatic dynamic kinetic resolution of beta-halo alcohols. An efficient route to chiral epoxides.
Enzymatic resolution of beta-chloro alcohols in combination with ruthenium-catalyzed alcohol isomerization led to a successful dynamic kinetic resolution (conversion up to 99% and ee up to 97%). The efficiency of the DKR is dramatically reduced when beta-bromo alcohols are used. The presence of the bromo substituent causes decomposition of the ruthenium catalysts, which triggers the progressive deactivation of the enzyme. The synthetic utility of this procedure has been illustrated by the practical synthesis of different chiral epoxides.
Pàmies
Oscar
O
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Sweden.
Bäckvall
Jan-E
JE