Tetrahedron p. 14177 - 14188 (1996)
Update date:2022-08-05
Topics: Characterization Catalyst Reactants Workup and Isolation Reaction Conditions
Takemoto, Yoshiji
Kuraoka, Satoru
Hamaue, Naoko
Aoe, Keiichi
Hiramatsu, Hajime
Iwata, Chuzo
A series of chiral enantiomerically pure 2-aryloxazolines was synthesized. (4S)-2-(2',6'-dimethoxyphenyl)-4-isopropyloxazoline proved to be an efficient chiral ligand for the Cu-catalyzed conjugate addition of Me3Al to cyclohexadienone, and by using 20 mol% of this ligand, 1,4-adduct was obtained in 68% ee. In addition, TBDMSOTf is crucial for the asymmetric conjugate addition to proceed with good chemical yield and high ee.
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