title: Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center.
abstract: Stereospecific substitutions of optically pure 1-(pyridinyl)ethyl methanesulfonates with various amines are described. The reaction of (R)- or (S)-1-(2-pyridinyl)ethyl methanesulfonate with primary amines, including amino acid esters, gives N-substituted (S)- or (R)-1-(2-pyridinyl)ethylamines (4) with inversion of the configuration. Secondary cyclic amines are also reacted with (R)-2 to give the corresponding substituted amines (5) in excellent yields. Optically pure and meso triamine ligands having two pyridine rings, (S,S)-4f and meso-4f, (S,S)-9e, (S,R)-9e, and (S,S)-9f, have been prepared in stereochemically pure form by this method. Not only the substitution reaction of optically active 2 but also that of 1-(4-pyridinyl)ethyl and 1-(3-pyridinyl)ethyl methanesulfonates 11 and 14 take place stereospecifcally with inversion of the chiral center.
authors.affiliation: Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan. juenishi@mb.kyoto-phu.ac.jp
authors.forename: Jun'ichi
authors.initials: J
authors.lastname: Uenishi
authors.forename: Masahiro
authors.initials: M
authors.lastname: Hamada
authors.forename: Sachiko
authors.initials: S
authors.lastname: Aburatani
authors.forename: Katsuya
authors.initials: K
authors.lastname: Matsui
authors.forename: Osamu
authors.initials: O
authors.lastname: Yonemitsu
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Tsukube