Absolute configurations of N,N-dialkyl α-amino acids and β-amino alcohols from exciton-coupled circular dichroism spectra of Cu(II) complexes

Organic Letters

Volumn 1, Issue 6, 1999, Pages 861-864

  Zahn, Steffen ^a   Canary, James W ^a  

^a NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; AMINOALCOHOL; COPPER;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM;

AMINO ACIDS; AMINO ALCOHOLS; CIRCULAR DICHROISM; COPPER;

EID: 0033598235     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990715a     Document Type: Article

References (25)

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15. Spartan 4.0 is available from Wavefunction, Inc., 18401 Von Karman Ave., Ste. 370, Irvine, CA 92612.
16. The spectroscopic data were consistent with the desired structures. Some overalkylation of amino acids with nucleophilic side chains (e.g., Lys, Cys) was observed.
17. Recorded on an AVIV 62A DS instrument. The concentration of the N,N-bis(2-quinaldyl) derivative was determined by UV-vis.
18. The free ligands did not yield ECCD spectra, but gave only simple CD spectra of greatly reduced amplitude.
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23. Glycine and proline were excluded. Threonine gave an ECCD spectrum but with opposite sign, possibly due to the presence of a second chiral center.
24. Nakanishi, K.; Berova, N. In Circular Dichroism: Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds.; VCH Publishers: New York, 1994; p 361.
25. 4SCN resulted in extraction of the Cu(II) ion from the ligand, evidenced by loss of amplitude and the ECCD features in the spectra.