Available online www.jocpr.com Journal of Chemical and Pharmaceutical Research, 2015, 7(7):283-288 Research Article ISSN : 0975-7384 CODEN(USA) : JCPRC5 283 Asymmetric synthesis and spectroscopic characterization of various N-substituted phthaloyl and tosyl derivatives Ghada Lahouar a , Ridha Touati a* , Sonia Khamri a , Jérôme Marrot b and Béchir Ben Hassine a a Laboratoire de Synthèse Organique Asymétrique et Catalyse Homogène (11URES56), Faculté des Sciences de Monastir, Université de Monastir, Bd. de l’Environnement, 5019 Monastir, Tunisia b Institut Lavoisier de Versailles ILV-UMR CNRS 8180, Université de Versailles Saint-Quentin en Yvelines, 45 avenue des Etats Unis, F-78035 Versailles, France _____________________________________________________________________________________________ ABSTRACT A convenient and efficient synthesis of series of new optically pure N-substituted α-amino esters starting from 2- methoxy-4-(2-propenyl) phenol (eugenol) and natural amino acids is described. This improved procedure offers a convenient and effective method to access some interesting molecules containing phthalimide, tosyl and alkenes functionalities. Keywords: Amino acids, phthalimide analogues, eugenol, tosyl derivatives, alkenes. _____________________________________________________________________________________________ INTRODUCTION Imide group is an interesting functionality, due to its wide presence in the natural products and in the pharmacologically active compounds. The specific reactivity of imides is a result of the relative acidity of the N group, a direct consequence of the presence of the two carbonyl groups [1]. Phthalimide derivatives are of particular biological interest and have been reported as herbicides, insecticides, antipsychotics and anti-inflammatory agents [2]. Substituted phthalimides are used predominantly as chiral building blocks in organic synthesis and can be used as key intermediates in the preparation of bio-active compounds i.e. antibacterial analgesic, antifungal, virucidal, plant growth regulator and also in dye industry [3]. Compounds containing phthalimide moiety are distinguished by their potent fungicidal action [4-6]. The well known products namely, folpet 1: [N-(trichloro methyl) thiophthalimide and compound 2 with enhanced activity against Tripanosoma cruzi). On the other hand, tosyl derivatives were also found to possess biological activity [7], among them are: perindopril tosylate 3 which was indicated as substitution therapy for treatment of essential hypertension [8], cholesteryl tosylate [9] and cis-tosylate [10]: intermediate of ketoconazole. In addition to that, alkenes group is an interesting functionality and they have long intrigued organic chemists because they are motifs of many natural products such as compound 4, [11-13] and usually served as substrates or intermediates in countless transformations. [14-16] Indeed, the synthesis of pure olefins is often a key step during the synthesis of important substances such as pheromones [17] or other natural products. [18]