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

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
› Author Affiliations
This work was supported by the grant of the Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/2018).
Further Information

Publication History

Received: 18 May 2018

Accepted after revision: 02 June 2018

Publication Date:
19 July 2018 (online)


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