Collect. Czech. Chem. Commun. 2005, 70, 1397-1410

Asymmetric Synthesis of (S)-2-Amino-3-(1-naphthyl)propanoic Acid via Chiral Nickel Complex. Crystal Structure, Circular Dichroism, 1H and 13C NMR Spectra of the Complex

Alexander Popkova,*, Ivana Císařováb, Jana Sopkovác, Josef Jirmand, Antonín Lyčkae and Konstantin A. Kochetkovf,*

a Faculty of Health and Social Studies, University of South Bohemia, 370 01 České Budějovice, Czech Republic
b Department of Inorganic Chemistry, Faculty of Natural Sciences, Charles University, Hlavova 2030, 128 40 Prague 2, Czech Republic
c UFR des Sciences Pharmaceutiques, 5 rue Vaubénard, 14032 Caen, France
d Research Institute for Pharmacy and Biochemistry, U Kabelovny 130, 102 37 Prague 10, Czech Republic
e Research Institute for Organic Syntheses, Rybitví 296, 532 18 Pardubice 20, Czech Republic
f A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Street 28, 117813 Moscow, Russia


The recently published environmentally friendly preparation of a glycine synthon 2 from regeneratable chiral auxiliary BPB ((S)-N-(2-benzoylphenyl)-N'-benzylprolinamide) was used for preparative asymmetric synthesis of the non-coded amino acid 3-(1-naphthyl)alanine (1). Full assignment of 1H and 13C NMR of both intermediate complex 3 and 1 and X-ray structure determination of complex 3 were made. Cotton effects observed in circular dichroism spectrum of complex 3 are consistent with published empirical rules.

Keywords: Amino acids; Biomimetic synthesis; BPB; Circular dichroism; Chiral auxiliaries; Crystal structure determination; Naphthylalanine; Nickel; NMR spectroscopy; Schiff bases.

References: 64 live references.