Chemoenzymatic synthesis of all four diastereomers of 2,6-disubstituted piperidines through stereoselective monoamination of 1,5-diketones.

@article{Simon2013ChemoenzymaticSO,
  title={Chemoenzymatic synthesis of all four diastereomers of 2,6-disubstituted piperidines through stereoselective monoamination of 1,5-diketones.},
  author={R. C. Simon and Ferdinand Zepeck and W. Kroutil},
  journal={Chemistry},
  year={2013},
  volume={19 8},
  pages={
          2859-65
        }
}
  • R. C. Simon, Ferdinand Zepeck, W. Kroutil
  • Published 2013
  • Chemistry, Medicine
  • Chemistry
  • The regioselectivity of various enantiocomplementary ω-transaminases was evaluated for the stereoselective monoamination of designated 1,5-diketones; excellent conversions, enantio- and regioselectivities were observed. The resulting amino-ketones underwent spontaneous intramolecular ring closure to afford Δ1-piperideines, which served as precursors for the cis- and anti-piperidine scaffold as demonstrated for the synthesis of the alkaloids dihydropinidine and epi-dihydropinidine. Key to the… CONTINUE READING
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