Tetrahedron p. 6453 - 6464 (1999)
Update date:2022-08-04
Topics:
Kohara, Takehiro
Hashimoto, Yukihiko
Saigo, Kazuhiko
A chiral amine; 1-(2,5-dimethoxyphenyl)ethylamine, was found to be an effective chiral auxiliary for the diastereoselective alkylation of its aldimines with alkylmetals. The 1-(2,5-dimethoxyphenyl)ethyl group of the chiral auxiliary could be removed by the acetylation and then oxidation of the resultant alkylated product, accompanying an amino-transfer from the chiral auxiliary to the final product. Racemic 1-(2,5- dimethoxyphenyl)ethylamine could be easily synthesized from 1,4- dimethoxybenzene and resolved by the diastereomeric salt formation with mandelic acid to give both enantiomers in pure forms.
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