Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1348238 | Tetrahedron: Asymmetry | 2006 | 5 Pages |
A new modified BINOL, (S)-3-[(1H-1,2,4-triazol-1-yl)methyl]-1,1′-binaphthol, was prepared. In the presence of titanium tetraisopropoxide, this ligand showed moderate catalytic properties for the asymmetric addition of diethylzinc to aldehydes. By treating rac-3-[(1H-1,2,4-triazol-1-yl)methyl]-1,1′-binaphthol with excess titanium tetraisopropoxide, a novel trinuclear titanium(IV) complex was obtained. A C3 axis along Ti1–Ti2–Ti3 is present in the molecule.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(S)-3-[(1H-1,2,4-Triazol-1-yl)methyl]-2,2′-bis(methoxymethyl)-1,1′-binaphtholC27H25N3O4Ee = 100%[α]D25=-56.6 (c 1.4, CH2Cl2)Source of chirality: resolutionAbsolute configuration: S
(S)-3-[(1H-1,2,4-Triazol-1-yl)methyl]-1,1′-binaphtholC23H17N3O2Ee = 100%[α]D25=-29.3 (c 0.3, CH2Cl2)Source of chirality: resolutionAbsolute configuration: S