| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1350400 | Tetrahedron: Asymmetry | 2007 | 4 Pages |
A new tertiary pseudo C2-symmetric diamine derived from (1S,2S)-(+)-pseudoephedrine was synthesized and tested in the enantioselective addition of methyllithium on different aromatic imines. A comparative study with a similar C2-symmetric ligand derived from the cyclohexane diamine showed better reactivity and enantioselectivity up to 91%.
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(1S,2S)-N1,N2-Bis(3,3-dimethylbutyl)-N1,N2-dimethyl-1-phenylpropane-1,2-diamineC23H42N2Ee = 99%[α]D20=+36.2 (c 0.97, CHCl3)Source of chirality: (+)-pseudoephedrinAbsolute configuration: (1S,2S)
(S)-N-(1-(Furan-3-yl)ethyl)-4-methoxybenzenamineC13H15NO2Ee = 75%[α]D20=-14.7 (c 1.04, CHCl3)Source of chirality: asymmetric synthesisAbsolute configuration: (S)
