One-pot formation of 2,4-di- or 2,4,6-tri-olefinic monocarboxylic acids by straight chain C4-extension

Jessica Sobotta; Maximilian Schmalhofer; Thomas M Steiner; Wolfgang Eisenreich; Günter Wächtershäuser; Claudia Huber

doi:10.1016/j.heliyon.2017.e00368

One-pot formation of 2,4-di- or 2,4,6-tri-olefinic monocarboxylic acids by straight chain C4-extension

Heliyon. 2017 Jul 27;3(7):e00368. doi: 10.1016/j.heliyon.2017.e00368. eCollection 2017 Jul.

Authors

Jessica Sobotta¹, Maximilian Schmalhofer¹, Thomas M Steiner¹, Wolfgang Eisenreich¹, Günter Wächtershäuser², Claudia Huber¹

Affiliations

¹ Lehrstuhl für Biochemie, Technische Universität München, Lichtenbergstraße 4, Garching D-85747, Germany.
² 2209 Mill Race Drive, Chapel Hill, NC 27514, USA.

Abstract

We report a one-pot formation of 2,4-diolefinic or 2,4,6-triolefinic monocarboxylic acids, R-(CH[bond, double bond]CH)_2or3-COOH, by decarboxylative condensation of an optionally α,β-unsaturated aldehyde with glutaconic acid, HOOC-CH₂-CH[bond, double bond]CH-COOH as straight chain C4-extender. The reaction is broadly applicable to saturated and unsaturated aldehydes and opens up a simple gateway to valuable organic products and reactive intermediates.

Keywords: Organic chemistry.