Stereo/regio-controlled cyclization of polychlorohex-5-enoic acids into substituted cyclobutanes

Synthesis of new derivatives of functionally substituted cyclobutanecarboxylic acids as potential neuromodulators

“…It should be noted that as opposed to the earlier obtained analogue of cyclobutane structures [4], in mass-spectrum of 3 ester (1-Phenylprop-2-yn-1yl) we can observe molecular-ion picks of minor intensity (2%). We thought that with the increase of molecular mass of investigated carbocycles, the relative stability of the observed substances to ionizing impact will increase too.…”

“…It was determined that the stereoisomeric composition of the cyclobutane derivatives depended on the nature of the functional groups in the initial dichloroalkenoic acids and was featured to involve in the coordination sphere of transition metals ion [4].…”

“…The structure of synthesized new derivatives of cyclobutane series 3 and 4 was established from the data of NMR spectra and via comparison of appropriate spectral characteristic of analogue cyclobutane scaffoldings [4]. These data obviously showed that the derivitization of cyclobutane carboxylic acid chloride 3 proceeded without any epimerization of 3 chiral centers in the cyclobutane ring.…”

“…From this point of view, elaboration of new technologies for the synthesis of cyclobutanecarboxylic acids with different structure modifications is a very important task. In our laboratory the generic method for construction of substituted cyclobutanecarboxylic acids was developed based on transition metal-catalyzed intramolecular cyclization reaction of -halogen-containing alkenoic acids via Atom Transfer Radical Cyclization (ATRC) [4] (Scheme 1).…”