4.8 Article

Stereodivergent entry to β-branched β-trifluoromethyl α-amino acid derivatives by sequential catalytic asymmetric reactions

Journal

CHEMICAL SCIENCE
Volume 12, Issue 30, Pages 10233-10241

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d1sc01442k

Keywords

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Funding

  1. University of Bologna (RFO program)
  2. MIUR (FFABR 2017)
  3. F.I.S. (Fabbrica Italiana Sintetici)

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This study presents a one-pot approach to enantioenriched beta-branched beta-trifluoromethyl alpha-amino acid derivatives, grounded on the reduction - ring opening of Erlenmeyer-Plochl azlactones. The configurations of the two chirality centers of the products are established during each of the two catalytic steps, enabling a stereodivergent process.
Currently, conventional reductive catalytic methodologies do not guarantee general access to enantioenriched beta-branched beta-trifluoromethyl alpha-amino acid derivatives. Herein, a one-pot approach to these important alpha-amino acids, grounded on the reduction - ring opening of Erlenmeyer-Plochl azlactones, is presented. The configurations of the two chirality centers of the products are established during each of the two catalytic steps, enabling a stereodivergent process.

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