Journal of Molecular Catalysis A: Chemical 274 (2007) 109–115 Aluminum tris (dodecyl sulfate) trihydrate Al(DS) 3 ·3H 2 O as an efficient Lewis acid–surfactant-combined catalyst for organic reactions in water Efficient conversion of epoxides to thiiranes and to amino alcohols at room temperature Habib Firouzabadi ∗ , Nasser Iranpoor ∗ , Abbas Khoshnood Department of Chemistry, Shiraz University, Shiraz 71454, Iran Received 4 April 2007; received in revised form 26 April 2007; accepted 26 April 2007 Available online 3 May 2007 Abstract High yielding preparation of structurally different thiiranes, -amino alcohols and bis(-amino) alcohols from the reaction of epoxides with thiourea and amines in the presence of catalytic amounts of aluminum tris (dodecyl sulfate) trihydrate Al(DS) 3 ·3H 2 O as a Lewis acid–surfactant- combined catalyst at room temperature in water has been described. Ring opening of epoxides with amines in the presence of this catalyst proceeded with high chemo- and regioselectivity. © 2007 Elsevier B.V. All rights reserved. Keywords: Aluminum tris (dodecyl sulfate) trihydrate; Water; Epoxide; Thiirane; Thiourea; Amio alcohol; Chemoselective reaction; Regioselective reaction 1. Introduction Nowadays, environmental consciousness encourages replacement of hazardous organic solvents with water which is a relatively green and a cheap media for organic reactions [1–11]. Along this line, we have studied Michael addition of amines and thiols to ,-unsaturated ketones [9], regioselective iodination of aromatic compounds with NaI/Ce(OH) 3 O 2 H [12] and ring opening of epoxides with different nucleophiles in water catalyzed by micellar solution of sodium dodecyl sulfate (SDS) [13]. We have recently reported oxidation of sulfides to their sulfoxides by H 2 O 2 in the presence of the in situ generated dodecyl hydrogen sulfate [14]. We have also reported aluminum tris (dodecyl sulfate) trihydrate [Al(DS) 3 ·3H 2 O] as an efficient Lewis acid–surfactant-combined catalyst for Michael addition of indoles and pyrrole to ,-unsaturated electron-deficient compounds in water [15]. ∗ Corresponding authors. Tel.: +98 711 2280926; fax: +98 711 2286008. E-mail addresses: firouzabadi@chem.susc.ac.ir (H. Firouzabadi), iranpoor@chem.susc.ac.ir (N. Iranpoor). Epoxides are small molecules with vast synthetic applica- tions. They are able to react with various nucleophiles and their potential to undergo regioselective ring opening reactions adds to their importance as highly useful precursors for the synthesis of organic compounds. Transformation of epoxides to their cor- responding thiiranes is a useful reaction [16,17]. Thiirane is the simplest heterocyclic ring system which carrying a sulfur atom in the ring and is found in naturally occurring compounds, her- bicides, pesticides, polymeric compounds, pharmaceuticals and in many other useful man-made chemicals [18]. For the prepa- ration of thiiranes from epoxides, variety of methods have been employed and reported in the literature [19–43]. Preparation of thiiranes from epoxides in water as the reaction media using an ionic liquid with KSCN [44], -cyclodextrin as a catalyst with KSCN or thiourea in water [45,46] and also synthesis of thi- irane in micellar solution of sodium dodecyl sulfate (SDS) in the presence of catalytic amounts of Ce(OTf) 4 has been recently reported [13]. -Amino alcohols are important intermediates for the syn- thesis of a vast range of biologically active natural and synthetic products, for the synthesis of amino acids, and also used as chi- ral auxiliaries/ligands for asymmetric synthesis [47–56]. One of the most accessible synthetic procedures for the preparation of 1381-1169/$ – see front matter © 2007 Elsevier B.V. All rights reserved. doi:10.1016/j.molcata.2007.04.035