Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center

The Journal of Organic Chemistry
Jun'ichi UenishiHiroshi Tsukube

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.

References

Feb 1, 1983·Journal of Medicinal Chemistry·F HavivP R Young

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Citations

Sep 30, 2015·Chemistry, an Asian Journal·Sakthi RajeRaja Angamuthu
Sep 4, 2009·The Journal of Organic Chemistry·Patrik KrumlindeJan-E Bäckvall
Jul 23, 2008·Organic Letters·Jonathan Clayden, Ulrich Hennecke
Apr 12, 2019·The Journal of Organic Chemistry·Vladislav SkrypaiMarc J Adler
Nov 9, 2019·Journal of the American Chemical Society·Yury LebedevMagnus Rueping
Apr 25, 2012·The Journal of Organic Chemistry·Manjinder S LallH D Hollis Showalter
Aug 30, 2018·The Journal of Organic Chemistry·Zhentao PanWeihui Zhong

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