Chiral building blocks for the synthesis of nitrogen??containing natural products, 5. The enantioselective synthesis of optically active, benzene nucleus??substituted 1?? …

G Bringmann, JP Geisler, T Geuder…

Index: Bringmann, Gerhard; Geisler, Joerg-Peter; Geuder, Torsten; Kuenkel, Georg; Kinzinger Lioba Liebigs Annalen der Chemie, 1990 , # 8 p. 795 - 805

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Citation Number: 16

Abstract

Abstract An efficient two-step procedure for the synthesis of enantiomerically pure, benzene nucleus-substituted 1-phenylethylamines 1 is described, with predictable absolute configuration at the stereogenic center: Imine formation from the substituted acetophenones 6 with (S)-or (R)-1-phenylethylamine [(S)-7 or (R)-7] and subsequent hydrogenation of the resulting Schiff bases 8 over Raney nickel leads to the secondary amines 9 and 10 in high ...