Facile synthesis of 1,3-oxathiolanes from ketones and i-mercaptoethanol

Sulfonic acid-functionalized ordered nanoporous Na+-montmorillonite as an efficient, eco-benign, and water-tolerant nanoreactor for chemoselective oxathioacetalization of aldehydes

“…Evaporation of the solvent followed by column chromatography on neutral silica gel gave the requested 1,3-oxathiolan in excellent yields. All the data (IR and 1 H NMR spectra) recorded are identical with the authentic samples and the reported methods [7][8][9][10][11][12][13][14][15]. …”

“…Moreover, the use of oxathiolanes is much more convenient than the corresponding O,O-acetals or S,S-acetals because they are comparatively more stable than O,O-acetals under acidic conditions and easier to remove than the corresponding S,S-acetals. A variety of Lewis acids including ZrCl 4 [7], Sc(OTf ) 3 [8], In(OTf ) 3 [9], LiBF 4 [10], Fe(CF 3 CO 2 ) [11], Fe(CF 3 SO 3 ) [11], BF 3 .OEt 2 [12], ZnCl 2 [13], MoO 2 (acac) 2 [14], and LaCl 3 [15] are used for the preparation of 1,3-oxathiolanes. However, moisture sensitivity of the majority of this type of reagents renders them unsuitable for use in large-scale applications.…”

Five‐Membered Heterocycles with Two Heteroatoms: O and S Derivatives

“…Several catalysts have been used for this reaction -the most common is BF 3 ÁEt 2 O [263]. More recently, other catalysts used for this reaction include triisopropyl triflate [264], indium triflate [265], NBS [266], tetrabutylammonium tribromide [267] and scandium triflate [268].…”

Nitroaromatic bis(2-hydroxyethyl)dithioacetals and oxathioacetals using 2-mercaptoethanol in the presence of chlorosilanes

“…13 Thus, urgency of the development of novel and efficient methods for the preparation of oxathio-and dithioacetals is due to the growth of their synthetic and practical usage. It is known that synthesis of the oxa-and thioacetals from carbonyl compounds proceeds via the catalysis with proton acids, 14,15 Lewis acids, [16][17][18][19][20] ets. 21,22 Some of these methods possess a low chemoselectivity, require hard reaction conditions, utilization of expensive or toxic catalysts and reagents, inert gas environment, long reaction time or an additional and complicated processing of the reaction mixture when the final products are separated.…”