The enantioselective synthesis of chiral diarylmethanols
is highly
desirable in synthetic chemistry and the pharmaceutical industry,
but it remains challenging, especially in terms of green and sustainable
production. Herein, a resin-immobilized palladium acetate catalyst
was fabricated with high activity, stability, and reusability in Suzuki
cross-coupling reaction of acyl halides with boronic acids, and the
coimmobilization of alcohol dehydrogenase and glucose dehydrogenase
on resin supports was also conducted for asymmetric bioreduction of
diaryl ketones. Experimental results revealed that the physicochemical
properties of the resins and the immobilization modes played important
roles in affecting their catalytic performances. These two catalysts
enabled the construction of a chemoenzymatic cascade for the enantioselective
synthesis of a series of chiral diarylmethanols in high yields (83–90%)
and enantioselectivities (87–98% ee). In addition, the asymmetric
synthesis of the antihistaminic and anticholinergic drugs (S)-neobenodine and (S)-carbinoxamine was
also achieved from the chiral diarylmethanol precursors, demonstrating
the synthetic utility of the chemoenzymatic cascade.