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Synthesis of syn-vicinal diamines via the stereoselective allylation of acyclic chiral α-amino aldimines

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Abstract The stereoselective allylation of acyclic chiral α-amino aldimines affording vicinal diamines, mediated by various Lewis acids (TiCl4, SnCl4, MgBr2·OEt2, BF3·OEt2, ZnCl2), is described. The TiCl4-mediated allylation of an α-N-Boc… Click to show full abstract

Abstract The stereoselective allylation of acyclic chiral α-amino aldimines affording vicinal diamines, mediated by various Lewis acids (TiCl4, SnCl4, MgBr2·OEt2, BF3·OEt2, ZnCl2), is described. The TiCl4-mediated allylation of an α-N-Boc aldimine afforded the allylation product with syn-selectivity, which in turn was used for the synthesis of an intermediate of an oseltamivir derivative.

Keywords: allylation acyclic; amino aldimines; allylation; stereoselective allylation; chiral amino; acyclic chiral

Journal Title: Tetrahedron Letters
Year Published: 2019

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