Direction of kinetically versus thermodynamically controlled organocatalysis and its application in chemoenzymatic synthesis

Abstract

The catalyst loading in the narrow range between 0.5 and 10 mol% determines whether an enantioselective organocatalytic aldol reaction proceeds under kinetic or thermodynamic control; high conversions and ee values can be achieved with low catalyst loadings (see scheme). Since the reaction is carried out in water, it can be combined with a biocatalytic reduction for the one-pot synthesis of 1,3-diols with d.r. >25:1 and 99% ee. © 2011 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.