Abstract

The synthesis of functionalized α,β-unsaturated sulfonamides by means of cross-metathesis of vinyl sulfonamides and olefins has been developed. The reaction proceeds smoothly in the presence of Hoveyda–Grubbs catalyst and its nitro analogue, providing a wide range of substituted products. The usefulness of this methodology has been proven in the preparation of new derivatives of biologically active ingredients, moxifloxacin and naratriptan.

Highlights

  • The synthesis of functionalized α,β-unsaturated sulfonamides by means of cross-metathesis of vinyl sulfonamides and olefins has been developed

  • A number of challenges were noted in the crossmetathesis reaction of α,β-unsaturated partners containing sulfur at various oxidation states.[4]

  • In contrast to allyl sulfides, vinyl sulfides are much less reactive, which is generally assumed with their ability to arrest

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Summary

Corresponding Authors

Łukasz Wozń iak − Institute of Organic Chemistry, Polish Academy of Sciences, 01-224 Warsaw, Poland. Rajkiewicz − Laboratory of Organometallic Synthesis, Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, 02-089 Warsaw, Poland. Louis Monsigny − Laboratory of Organometallic Synthesis, Biological and Chemical Research Centre, Faculty of Chemistry, University of Warsaw, 02-089 Warsaw, Poland; orcid.org/ 0000-0001-9325-1316.

■ ACKNOWLEDGMENTS
Findings
■ REFERENCES

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