Facile synthesis of optically pure 1,2-diaryl (and 1-Alkyl-2-aryl) ethyl and propylamines |
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Authors: | García Ruano José L Alemán José Soriano José F |
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Affiliation: | Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. joseluis.garcia.ruano@uam.es |
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Abstract: | A concise high-yielding route to synthetically useful 1,2-diaryl (and 1-alkyl-2-aryl) ethyl and propylamines in high enantiomeric purity is described. The key step of this route is the completely stereoselective addition of lithium (R)-ortho-(p-toluenesulfinyl)benzylic carbanions to (S)-N-p-toluenesulfinylimines, which takes place in very high or quantitative yields. N-Desulfinylation and C-desulfinylation of the resulting adducts can be achieved with no loss of optical purity employing conventional methods (TFA and Raney-Ni, respectively). |
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