An unusual chemoselectivity in cobalt(II) chloride catalysed cleavage of oxiranes with anilines: A highly regioselective synthesis of β-amino alcohols

Double Metal Cyanides as Efficient Solid Acid Catalysts for Synthesis of β-Amino Alcohols Under Solvent-Free Conditions

“…Selectivity for the A-isomer is higher in most of the cases (Table 1). The intrinsic catalytic activity (turnover frequency; TOF) of Fe-Zn double metal cyanide catalysts is higher than most of the known catalysts for this reaction [6][7][8][9][10][11]. For the reaction between styrene oxide and aniline conducted under similar conditions, the TOF values over sulfamic acid, amberlyst-15, Sc(OTf) 3 , NaY, SBA-15-pr-SO 3 H and Ti-MCM-41 catalysts were 32, 2, 7, 0.8, 68 and 169 h -1 , respectively [6][7][8][9][10][11]13].…”

“…A large number of promoters and catalyst system have been reported, e.g. sulfamic acid [6], Amberlyst-15 [7], metal amides, metal triflates [8], transition metal halides [9], ionic liquids [10], and Lewis acids [11]. However, all those required long reaction times, elevated temperatures, high pressures and stoichiometric amounts of catalyst.…”

Hβ zeolite: An Efficient and Reusable Catalyst for Ring-Opening of Epoxides with Amines Under Microwave Irradiation

“…Therefore, the development of new methods for the nucleophilic ring-opening of epoxides that work under mild conditions is of great importance. In this direction various Lewis acid promoters viz., metal halides [6][7][8][9], metal triflates [10][11][12][13], metal alkoxides [14], metal amides and triflamide [15][16][17], transition metal salts [18], hexafluoro-2-propanol under reflux (HFIP) [19], ionic liquid [20], zirconium sulfophenyl phosphonate [21], sulphated zirconia [22], silica [23], alumina/modified alumina [24,25] and montmorillonite clay were used as catalysts at room temperature/microwave irradiation [26] in the presence/absence of a solvent [27]. The reactions proceed smoothly to give the b-aminoalcohol in good to excellent yields.…”

H14[NaP5W29MoO110]: a Novel and Useful Catalyst for Aminolysis of Epoxides with Amines under Solvent‐Free Conditions

“…2 The nucleophilic ring-opening of epoxides with an amine is recognized as an important route to obtain β-amino alcohol with 1,2-trans stereochemistry. Therefore, various methodologies have been developed for this purpose, which include the use of alumina, 3 metal alkoxides, 4 metal triflates, [5][6][7] transition metal halides, 8 alkali metal perchlorates, 9 rare earth metal halides, 10 silica under high pressure, 11,12 and montmorillonite clay under microwave irradiation. 13 However, these methodologies suffer from one or more disadvantages such as long reaction time, high reaction temperature, moderate yield, use of air or moisture sensitive catalysts, and requirement of the stoichiometric amount of catalyst.…”