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Organic & Biomolecular Chemistry
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Journal Name
COMMUNICATION
9
catalytic activity of CALB was maintained through four reaction
cycles without significant loss in oxidation activity (99-94%
conversions of 5a, Figure 2). A drop to 39% of activity was
observed in the fifth cycle.28
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Conclusions
In conclusion, a novel, mild and selective methodology for the
synthesis of sulfoxide compounds in high yields was developed
using CALB biocatalyst and UHP. The oxidation of sulfide
substrates occurs exploiting AcOEt with a dual role of solvent
and CALB substrate in the generation of the peroxyacid reactive
intermediate 8a. Sulfide substrates bearing different functional
groups such as alkenes and carbonyls were also selectively
oxidised at the sulfur atom, proving the chemoselectivity of the
methodology over side reactions like epoxidations and Baeyer-
Villiger oxidations. The methodology was applied to the
synthesis of the drug omeprazole and investigated at gram scale
on the substrate 5a, showing excellent yields and E-factors.
These data, in addition to the robustness and the recyclability
of CALB biocatalyst, demonstrate the high translation potential
of this methodology for industrial applications.
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Conflicts of interest
There are no conflicts to declare.
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