A Wacker oxidation using CuCl/PdCl2 as a catalyst system was successfully combined with an enzymatic ketone reduction to convert styrene enantioselectively into 1-phenylethanol in a one-pot process, although the two reactions conducted in aqueous media are not compatible due to enzyme deactivation by Cu ions. The one-pot feasibility was achieved via compartmentalization of the reactions. Conducting the Wacker oxidation in the interior of a polydimethylsiloxane thimble enables diffusion of only the organic substrate and product into the exterior where the biotransformation takes place. Thus, the Cu ions detrimental to the enzyme are withheld from the reaction media of the biotransformation. In this one-pot process, which formally corresponds to an asymmetric hydration of alkenes, a range of 1-arylethanols were formed with high conversions and 98-99 % ee. In addition, the catalyst system of the Wacker oxidation was recycled 15 times without significant decrease in conversion.

to his 75th birthday As ac omplementary approach to current asymmetrics ynthetic methods, ad irect transformation of styrenes into 1-phenylethylamines was developed. The one-pot process represents af ormal hydroamination of an on-activated alkene with ammonia andi sb ased on the combination of aP d/Cu-catalyzed Wacker-oxidation with an enzymatic transamination.Akey feature of this processi st he compartmentation of the catalytic systems, which turned out to be essential to avoid deactivation of the transaminase by the Cu-component. This one-pot synthesis can be applied to ab road substrate range, which leads to the chiral amines with high conversionsa nd excellent enantioselectivities of > 99 % ee.

No abstract

PDMS thimble was the key to combining incompatible reactions to achieve deracemization of 1-phenylethanols in high yield with high optical yield.