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School of Biological and Chemical Sciences

Synthesis of chiral heterocycles through Pd-catalysed allylic alkylation processes

Project description

The Arseniyadis group is principally interested in the development of new synthetic tools to attain high structural and functional complexity. These methods span within the areas of organocatalysis, transition metal catalysis and, more recently, bio-hybrid catalysis. For the past several years, we have been interested in implementing the palladium-catalyzed asymmetric allylic alkylation (Pd-AAA) to the synthesis of a variety of chiral heterocycles including chiral isoxazolidin-5-ones, b-lactams, butenolides, furanones, butyrolactones, 4,5-dihydro pyrazoles and other diversely substituted 5‑, 6‑, 7-, 14- and 16‑membered ring  a‑phosphono oxaheterocycles all bearing quaternary stereogenic centers. The present project aims at applying the Pd-AAA to new pro-chiral substrates and ultimately apply the method to the synthesis of key enantioenriched building blocks and natural products. 

References

  1. Arseniyadis, S. et al. Org. Lett. 2019 (DOI: 10.1021/acs.orglett.9b03522).
  2. Arseniyadis, S.; Cossy, J. et al. Org. Lett. 201921, 603.
  3. Arseniyadis, S. et al. Org. Lett. 201921, 2231.
  4. Arseniyadis, S.; El Kaïm, L. et al. Adv. Synth. & Catal. 2018, 360, 449.
  5. Arseniyadis, S.; Cossy, J. et al. Chem. Eur. J201824, 4810.
  6. Arseniyadis, S.; Cossy, J. et al. Chem. Eur. J. 201824, 8076.
  7. Arseniyadis, S.; Cossy, J. et al. Org. Lett. 201719, 14.
  8. Arseniyadis, S.; Ilitki, H.; El Kaïm, L. et al. Chem. Commun. 2016, 52, 14490.
  9. Arseniyadis, S.; Cossy, J. et al. Synlett 2013, 2350.
  10. Arseniyadis, S.; Cossy, J. et al. Angew. Chem. Int. Ed201352, 1257.
  11. Arseniyadis, S.; Cossy, J. et al. Angew. Chem. Int. Ed. 201251, 7562.

See also