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Directed ortho-lithiation as a tool for synthesis of chiral 1,2-disubstituted arylsulfonamides

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Abstract

The directed ortho-lithiation is demonstrated as an excellent method for additional functionalization of chiral phenyl and naphthyl sulfonamides. The chirality was introduced through sulfonamide formation with a series of chiral amines prior to the lithiation process. In the case of naphthyl sulfonamides the regioselectivity of the directed ortho-lithiation was studied and optimized. The approach was shown to provide facile ortho-functionalization and was applied for the synthesis of chiral 1,2-sulfonamido phosphine derivatives. The latter were evaluated as P,O-ligands in Pd-catalyzed asymmetric allylic substitution.

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Notes

  1. Full particulars of experimental details and spectroscopic data of all compounds introduced in the preliminary report [22], which are not published yet, are given in the electronic supplementary material (ESI).

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Acknowledgements

This work was promoted by Bulgarian National Science Fund UNA-17/2005 and DRNF-02/13/2009. We thank Dr. Yavor Mitrev and Dr. Miroslav Dangalov for helpful discussions in respect of NMR experiments.

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Authors and Affiliations

  1. Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Science, Acad. G, Bonchev 9, 1113, Sofia, Bulgaria

    Martin Ravutsov, Zhanina Petkova & Vladimir Dimitrov

Authors
  1. Martin Ravutsov
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  2. Zhanina Petkova
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  3. Vladimir Dimitrov
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Correspondence to Vladimir Dimitrov.

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Supplementary material 1 (DOCX 713 kb)

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Ravutsov, M., Petkova, Z. & Dimitrov, V. Directed ortho-lithiation as a tool for synthesis of chiral 1,2-disubstituted arylsulfonamides. Monatsh Chem 149, 2207–2229 (2018). https://doi.org/10.1007/s00706-018-2296-6

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  • DOI: https://doi.org/10.1007/s00706-018-2296-6

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