New chiral polyfunctional cyclobutane derivatives from (-)-verbenone: Possible surfactant behaviour

New enantiopure cyclobutane derivatives have been synthesized from a chiral precursor derived from (-)-verbenone. The cyclobutane moiety acts as a chiral platform to afford a γ-amino acid function in a branched side-chain containing an additional stereogenic centre as well as additional C6 or C16-alkyl chains linked to the ring by means of an amine or an amide function. One of these compounds, obtained as a 1:2 mixture with its TFA salt has been investigated, suggesting behaviour as a good surfactant and its critical micellar concentration has been determined. © 2013 Elsevier Ltd. All rights reserved.Imma Carrera is acknowledged for help in the measurement of surface tensions. Jaume Caelles from the SAXS-WAXS service at IQAC is acknowledged for the SAXS measurements. The authors thank financial support from Spanish Ministerio de Ciencia e Innovación (grant CTQ2010-15408/BQU and CTQ2010-14897) and Generalitat de Catalunya (grant 2009SGR-733 and 2009SGR-1331).Peer reviewe