Full Papers
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The authors declare no conflict of interest.
Keywords: Apremilast · olefin metathesis · vinyl sulfones ·
styrenes · microwave
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Scheme 6. Small and larger scale synthesis of Apremilast (6) from β-sulfonyl
styrene 3aa. DMA=Dimethylacetamide.
[
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Conclusions
In conclusion, we have successfully developed an efficient
method to obtain functionalised β-sulfonyl styrenes from
various vinyl sulfones and styrenes or allylbenzenes using MW-
assisted cross-metathesis. Utilisation of one-pot isomerisation/
deuteration/cross-metathesis enabled to access β-deuterated
α,β-unsaturated sulfones from allylbenzenes. Finally, we have
successfully accomplished a highly efficient larger scale syn-
thesis of Apremilast and ent-Apremilast, which can be of
interest in pharmaceutical production.
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[14] One-pot strategies, involving olefin metathesis combined with other
chemical transformations are of interest in modern organic chemistry,
as it not only results the synthesis of numerous products easier and
cheaper way, but can also induce new concepts in synthetic planning.
For a review, see: G. K. Zieliński, K. Grela, Chem. Eur. J. 2016, 22, 9440–
9454.
Acknowledgements
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Authors are grateful to the „Catalysis for the Twenty-First Century
Chemical Industry” project carried out within the TEAM-TECH
programme of the Foundation for Polish Science co-financed by
the European Union from the European Regional Development
under the Operational Programme Smart Growth. The study was
carried out at the Biological and Chemical Research Centre,
University of Warsaw, established within the project co-financed
by European Union from the European Regional Development
Fund under the Operational Programme Innovative Economy,
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