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A Dimeric Thiourea CSA for the Enantiodiscrimination of Amino Acid Derivatives by NMR Spectroscopy.
Recchimurzo, Alessandra; Micheletti, Cosimo; Uccello-Barretta, Gloria; Balzano, Federica.
Afiliação
  • Recchimurzo A; Department of Chemistry and Industrial Chemistry, University of Pisa, via Moruzzi 13, 56124 Pisa, Italy.
  • Micheletti C; Department of Chemistry and Industrial Chemistry, University of Pisa, via Moruzzi 13, 56124 Pisa, Italy.
  • Uccello-Barretta G; Department of Chemistry and Industrial Chemistry, University of Pisa, via Moruzzi 13, 56124 Pisa, Italy.
  • Balzano F; Department of Chemistry and Industrial Chemistry, University of Pisa, via Moruzzi 13, 56124 Pisa, Italy.
J Org Chem ; 86(11): 7381-7389, 2021 06 04.
Article em En | MEDLINE | ID: mdl-34019407
ABSTRACT
The reaction of benzoyl isothiocyanate with (1R,2R)-1,2-bis(2-hydroxyphenyl)ethylenediamine afforded a new thiourea chiral solvating agent (CSA) with a very high ability to differentiate 1H and 13C NMR signals of simple amino acid derivatives, even at low concentrations. The enantiodiscrimination efficiency was higher with respect to that of the parent monomer, a thiourea derivative of 2-((1R)-1-aminoethyl)phenol, thus putting into light the relevance of the cooperativity between the two molecular portions of the dimer in a cleft conformation stabilized by interchain hydrogen bond interactions. An achiral base additive (DABCO or DMAP) played an active role in the chiral discrimination processes, mediating the interaction between the CSA and the enantiomeric mixtures. The chiral discrimination mechanism was investigated by NMR spectroscopy through the determination of complexation stoichiometries, association constants, and the stereochemistry of the diastereomeric solvates.
Assuntos

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Tioureia / Aminoácidos Idioma: En Revista: J Org Chem Ano de publicação: 2021 Tipo de documento: Article

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Tioureia / Aminoácidos Idioma: En Revista: J Org Chem Ano de publicação: 2021 Tipo de documento: Article