4.6 Article

omega-Transaminases as efficient biocatalysts to obtain novel chiral selenium-amine ligands for Pd-catalysis

Journal

ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 9, Pages 2043-2051

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/b920946h

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Funding

  1. CNPq
  2. CAPES
  3. FAPESP
  4. Province of Stryria
  5. Codexis
  6. FFG

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omega-Transaminases have been evaluated as biocatalysts in the reductive amination of organoselenium acetophenones to the corresponding amines, and in the kinetic resolution of racemic organoselenium amines. Kinetic resolution proved to be more efficient than the asymmetric reductive amination. By using these methodologies we were able to obtain both amine enantiomers in high enantiomeric excess (up to 99%). Derivatives of the obtained optically pure o-selenium 1-phenylethyl amine were evaluated as ligands in the palladium-catalyzed asymmetric alkylation, giving the alkylated product in up to 99% ee.

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