| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1345787 | Tetrahedron: Asymmetry | 2013 | 4 Pages |
The conjugate addition of S-, N- and O-heterocyclic nucleophiles to the CC bond of dehydroalanine, bonded as a Schiff’s base to the chiral auxiliary (S)-2-[N-(N′-benzylprolyl)amino]benzophenone in the coordination sphere of NiII, resulted in the asymmetric synthesis of novel (S)-α-aminopropionic acids containing a heterocyclic side chain, including imidazole, triazole, thiodiazole, thiazole and oxazole moieties (de 20–92%). After purification and cleavage of the metal complexes, the heterocyclic amino acids were isolated with high enantiomeric purity (ee >97%).
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(S)-2-Amino-3-(2-thioxobenzo[d]thiazol-3(2H)-yl)propanoic acidC10H10N2O2S2[α]D20=+33.8 (с 0.66, 2M HCl)Source of chirality: (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamideAbsolute configuration: l or (S)
(S)-2-Amino-3-(2-thioxobenzo[d]oxazol-3(2H)-yl)propanoic acidC10H10N2O3S[α]D20=+8.25 (с 1.09, 2M HCl)Source of chirality: (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamideAbsolute configuration: l or (S)
(S)-2-Amino-3-(3-methyl-2-thioxo-2,3-dihydro-H-imidazol-1-yl)propanoic acidC7H11N3O2S[α]D20=-1.9 (с 1.0, 2M HCl)Source of chirality: (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamideAbsolute configuration: l or (S)
(S)-2-Amino-3-(4-methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-1-yl)propanoic acidC6H10N4NiO2S[α]D20|=-25.0 (c 1.0, 2M HCl)Source of chirality: (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamideAbsolute configuration: l or (S)
(S)-2-Amino-3-(2-thioxothiazolidin-3-yl)propanoic acidC6H10N2O2S2[α]D20=-18.2 (с 0.72, 2 M HCl)Source of chirality: (S)-N-(2-benzoylphenyl)-1-benzylpyrrolidine-2-carboxamideAbsolute configuration: l or (S)
