Stereodivergent entry to β-branched β-trifluoromethyl α-amino acid derivatives by sequential catalytic asymmetric reactions
Vasco Corti, Riccardo Riccioli, Ada Martinelli, Sofia Sandri, Mariafrancesca Fochi, Luca Bernardi
Abstract
Currently, conventional reductive catalytic methodologies do not guarantee general access to enantioenriched β-branched β-trifluoromethyl α-amino acid derivatives. Herein, a one-pot approach to these important α-amino acids, grounded on the reduction - ring opening of Erlenmeyer-Plöchl 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.
Topics & Concepts
TrifluoromethylErlenmeyer flaskCatalysisChemistryRing (chemistry)Amino acidCombinatorial chemistryOrganic chemistryCatalytic hydrogenationChromatographyBiochemistryAlkylFluorine in Organic ChemistryAsymmetric Synthesis and CatalysisAsymmetric Hydrogenation and Catalysis