| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1347624 | Tetrahedron: Asymmetry | 2008 | 5 Pages |
The synthesis of (S)-2-amino-3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoate as the parent homologue of a novel generation of chiral NHC precursors is described. Crystallographic data for the novel chiral NiII complex, and Boc-protected amino acid containing imidazolium moiety are also given. The silver(I) carbene complex of the Boc-protected amino acid has been obtained.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
[(S)-2-({2-[(2S,1RN)-1-Benzylpyrrolidine-2-carboxamido]phenyl}(phenyl)methyleneamino)-3-(1H-imidazol-1-yl)propanoato-N,N′,N″,O] nickel(II)C31H29N5NiO3Ee >99%[α]D25=+2356 (c 0.050, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (RN,S,S)
({1-[(S)-2-({2-[(2S,1RN)-1-Benzylpyrrolidine-2-carboxamido]phenyl}(phenyl)methyleneamino)-2-carboxylato-N,N′,N″,O]-nickel(II)}ethyl)-3-methyl-1H-imidazol-3-ium tetrafluoroborateC32H32BF4N5NiO3Ee >99%[α]D25=+2386 (c 0.056, MeOH)Source of chirality: asymmetric synthesisAbsolute configuration: (RN,S,S)
(S)-2-Amino-3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoateC7H11N3O2Ee >99%[α]D25=-18.4 (c 1.4, H2O)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-2-(tert-Butoxycarbonylamino)-3-(3-methyl-1H-imidazol-3-ium-1-yl)propanoateC12H19N3O4Ee >99%[α]D25=+111.4 (c 1.02, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(1-(2-(tert-Butoxycarbonylamino)-2-carboxylatoethyl)-3-methyl-1H-imidazol-2-ylidene)silver(I)C12H18AgN3O4Ee >99%[α]D25=+60.0 (c 1.02, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
