Asymmetric synthesis of (S)-2-amino-3-(1-naphthyl)propanoic acid via chiral nickel complex. Crystal structure, circular dichroism, H-1 and C-13 NMR spectra of the complex

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 H-1...

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Published inCollection of Czechoslovak chemical communications Vol. 70; no. 9; pp. 1397 - 1410
Main Authors Popkov, A, Cisarova, Sopkova, J, Jirman, J, Lycka, A, Kochetkov, KA
Format Journal Article
LanguageEnglish
Published PRAGUE 6 Inst Organic Chem And Biochem 01.01.2005
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
chiral auxiliaries
nickel
Schiff bases
ALPHA-AMINO
ENANTIOSELECTIVE SYNTHESIS
MICHAEL ADDITION-REACTIONS
amino acids
(S)-2-(N-BENZYLPROLYL)AMINOBENZOPHENONE
ALDOL REACTIONS
STEREOSPECIFIC SYNTHESIS
NUCLEOPHILIC GLYCINE
circular dichroism
NI(II) COMPLEXES
DIASTEREOSELECTIVE SYNTHESIS
BPB
naphthylalanine
SCHIFF-BASE
crystal structure determination
NMR spectroscopy
biomimetic synthesis
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Summary: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 H-1 and C-13 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.
ISSN:0010-0765
1212-6950
DOI:10.1135/cccc20051397