Synthesis 2018; 50(20): 4081-4088
DOI: 10.1055/s-0036-1591598
paper
© Georg Thieme Verlag Stuttgart · New York

Expedient Synthesis of Long-Chain ω-Substituted Fatty Acids and Esters from Cyclic Ketones Using Iodine and Hydrogen Peroxide

Autoren

  • Ekaterina V. Podrezova

    a   The Tomsk Polytechnic University, Lenin avn., 30, 634050 Tomsk, Russian Federation   eMail: yusubov@mail.ru
  • Maria S. Larkina

    b   Siberian State Medical University, 634050 Tomsk, Russian Federation
  • Mikhail V. Belousov

    b   Siberian State Medical University, 634050 Tomsk, Russian Federation
  • Andreas Kirschning

    c   Institute of Organic Chemistry and Center of Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 301267 Hannover, Germany
  • Viktor V. Zhdankin*

    a   The Tomsk Polytechnic University, Lenin avn., 30, 634050 Tomsk, Russian Federation   eMail: yusubov@mail.ru
    d   Department of Chemistry and Biochemistry, University of Minnesota Duluth, MN 55812, USA
  • Mekhman S. Yusubov*

    a   The Tomsk Polytechnic University, Lenin avn., 30, 634050 Tomsk, Russian Federation   eMail: yusubov@mail.ru

This work was supported by the grant of the Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/2018).
Weitere Informationen

Publikationsverlauf

Received: 18. Mai 2018

Accepted after revision: 02. Juni 2018

Publikationsdatum:
19. Juli 2018 (online)


Graphical Abstract

Abstract

A simple and convenient synthesis of ω-iodoaliphatic carboxylic acids and esters by the reaction of cyclic ketones with iodine and hydrogen peroxide in the presence of catalytic CuCl has been developed. ω-Iodoaliphatic carboxylic esters were further used for the efficient preparation of di(2-pyridylmethylamino)alkanoic acids in excellent yields.

Supporting Information