| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350170 | Tetrahedron: Asymmetry | 2008 | 7 Pages |
Several chiral amino alcohols have been synthesized conveniently and effectively. 1H NMR was utilized to investigate their enantiodiscriminating abilities. Chiral amino alcohols 2 and 4 were discovered as efficient CSAs for the determination of the enantiomeric compositions of chiral carboxylic acids. In particular, for the Ts-derivatives of amino acids studied herein, 4 could be used for the assignment of the absolute configurations of the Ts-derivatives of amino acids with a neutral side chain through the chemical shift non-equivalences of their NH (Ts) protons with certain confidence.
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(S)-2-(5-Bromo-2-dimethylamino-benzylamino)-1,1,3-triphenyl-propan1-1-olC30H31N2OBr[α]D20=-41.6 (c 0.44, CHCl3)Source of chirality: l-phenylalanineAbsolute configuration: (S)
(S,S)-2-{[(2-Dimethylamino-5-methylphenyl)-naphthalen-1-ylmethyl]amino}-1,1,3-triphenyl-propan-1-olC41H40N2O[α]D20=+42.8 (c 0.50, CHCl3)Source of chirality: l-phenylalanineAbsolute configuration: (S,S)
(S,R)-2-{[(2-Dimethylamino-5-methylphenyl)-naphthalen-1-ylmethyl]amino}-1,1,3-triphenyl-propan-1-olC41H40N2O[α]D20=-34.9 (c 0.47, CHCl3)Source of chirality: l-phenylalanineAbsolute configuration: (S,R)
