231617-04-2Relevant articles and documents
Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines: Dual stereocontrol with nearly perfect diastereoselectivity
Zhao, Yi-Shuang,Liu, Qiang,Tian, Ping,Tao, Jing-Chao,Lin, Guo-Qiang
, p. 4174 - 4178 (2015)
Copper-catalyzed asymmetric allylation of chiral N-tert-butanesulfinyl imines has been described. Dual stereocontrol, through the combination of a chiral auxiliary and a chiral copper complex, has played an important role in achieving the nearly perfect d
Synthesis of enantiopure benzyl homoallylamines by indium-mediated barbier-type allylation combined with enzymatic kinetic resolution: Towards the chemoenzymatic synthesis of N-containing heterocycles
Hietanen, Ari,Saloranta, Tuna,Rosenberg, Sara,Laitinen, Evelina,Leino, Reko,Kanerva, Liisa T.
scheme or table, p. 909 - 919 (2010/04/23)
Barbier-type indium-mediated allylations of different N, N(dimethylsulfamoyl)-protected aldimines with a number of allyl bromides followed by high-yielding deprotection afforded allylic amines in good to excellent yields, The racemic amines were then subj
Design, synthesis, and optical resolution of a novel non-natural chiral auxiliary, 1-(2,5-dimethoxyphenyl)ethylamine. Application to diastereoselective alkylation of aldimines
Kohara, Takehiro,Hashimoto, Yukihiko,Saigo, Kazuhiko
, p. 6453 - 6464 (2007/10/03)
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.