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Uenishi J, Hamada M, Aburatani S, et al. Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center. J Org Chem. 2004;69(20):6781-9doi: 10.1021/jo0491758.
Uenishi, J., Hamada, M., Aburatani, S., Matsui, K., Yonemitsu, O., & Tsukube, H. (2004). Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center. The Journal of organic chemistry, 69(20), 6781-9. https://doi.org/10.1021/jo0491758
Uenishi, Jun'ichi, et al. "Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center." The Journal of organic chemistry vol. 69,20 (2004): 6781-9. doi: https://doi.org/10.1021/jo0491758
Uenishi J, Hamada M, Aburatani S, Matsui K, Yonemitsu O, Tsukube H. Synthesis of chiral nonracemic 1-(2-pyridinyl)ethylamines: stereospecific introduction of amino function onto the 2-pyridinylmethyl carbon center. J Org Chem. 2004 Oct 01;69(20):6781-9. doi: 10.1021/jo0491758. PMID: 15387603.
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J Org Chem. 2004 Oct 01;69(20):6781-9. doi: 10.1021/jo0491758.

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 Uenishi, Masahiro Hamada, Sachiko Aburatani, Katsuya Matsui, Osamu Yonemitsu, Hiroshi Tsukube

Affiliations

  1. Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8412, Japan. [email protected]

PMID: 15387603 DOI: 10.1021/jo0491758

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.

Copyright 2004 American Chemical Society

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