Collect. Czech. Chem. Commun. 1998, 63, 211-221

Axially Chiral Bis(α-amino Acid)s and Their Deamino Analogues. Synthesis and Configurational Assignment

Miloš Tichýa, Luděk Ridvana, Miloš Buděšínskýa, Jiří Závadaa, Jaroslav Podlahab and Ivana Císařováb

a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
b Department of Inorganic Chemistry, Charles University, 128 40 Prague 2, Czech Republic


The axially chiral bis(α-amino acid)s cis-2 and trans-2 as possible building blocks for polymeric structures of novel type of helicity were prepared. Their configuration has been determined by NMR spectroscopy and, in the case of the trans-isomer, confirmed by single-crystal X-ray diffraction. Analogous pair of stereoisomeric diacids cis-3 and trans-3, devoid of the amino groups, was also prepared and their configuration assigned. The observed differences in the NMR spectra of cis- and trans-isomers of 2 and 3 are discussed from the viewpoint of their different symmetry properties.

Keywords: Chiral bis(α-amino acid)s; Axial chirality; Amino acids; NMR spectrometry; X-Ray diffraction.