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

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Title: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
Creators:
Popkov, Alexander
Císařová, Ivana
Sopková, Jana
Jirman, Josef
Lyčka, Antonín
Kochetkov, Konstantin A.
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 70, 9, pp. 1397-1410
Uncontrolled Keywords:Chiral auxiliaries, Naphthylalanine, Crystal structure determination, BPB, Schiff bases, Biomimetic synthesis, Nickel, Amino acids, Circular dichroism, NMR spectroscopy

Abstract

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

Title: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
Creators:
Popkov, Alexander
Císařová, Ivana
Sopková, Jana
Jirman, Josef
Lyčka, Antonín
Kochetkov, Konstantin A.
Uncontrolled Keywords:Chiral auxiliaries, Naphthylalanine, Crystal structure determination, BPB, Schiff bases, Biomimetic synthesis, Nickel, Amino acids, Circular dichroism, NMR spectroscopy
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:70
Number:9
Page Range:pp. 1397-1410
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc20051397UNSPECIFIED
ID Code:2419
Item Type:Article
Deposited On:06 Feb 2009 17:18
Last Modified:06 Feb 2009 16:18

Citation

Popkov, Alexander; Císařová, Ivana; Sopková, Jana; Jirman, Josef; Lyčka, Antonín; Kochetkov, Konstantin A. (2005) 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. Collection of Czechoslovak Chemical Communications, 70 (9). pp. 1397-1410. ISSN 0010-0765

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