An efficient protocol for regioselective ring opening of epoxides using samarium triflate: Synthesis of propranolol, atenolol and RO363

A facile and efficient synthesis of β-amino alcohols using 2,2,2-trifluoroethanol as a metal-free and reusable medium

“…Several Lewis acids or Bronsted acids as a useful activator have been reported. That is, high to excellent regioselectivity of aminolysis of epoxides has been observed with Sn(OTf) 2 [16], Cu(OTf) 2 [16], Sm(OTf) 3 [17], Al(OTf) 3 [18], Er(OTf) 3 [19], InCl 3 [20], BiCl 3 [21], SbCl 3 [22], ZnCl 2 [23], InBr 3 [24], CoCl 2 [25], Cu(BF 4 ) 2 [26], Al 2 O 3 [27], ionic liquids [28], silica [29][30], sulfated zirconia [31] and Y(NO 3 ) 3 Á6H 2 O [32]. In general, efficient separation of the amino alcohol product from the Lewis acid catalyst used is often troublesome due to the emulsion formation under basic conditions at the aqueous work-up step.…”

Synthesis and stability of L-tryptophan adsorbed on Ti/MCM-41 as a catalyst for the regioselective aminolysis of styrene oxide

“…The aminolysis of epoxides is an acid-catalyzed reaction [13]. Among the catalysts reported for this type of reaction, Lewis acid catalysis is the most widely adopted method for epoxide ring openings with amines, e.g., BiCl 3 [14], VCl 3 [15], ZrCl 4 [16], Al(OTf) 3 [17], CoCl 2 [18], InBr 3 [19], Sc(OTf) 3 [20], Sm(OTf) 3 [21], and IrCl 3 [22]. However, the use of homogeneous Lewis acids could be problematic, because they may trigger an undesired isomerization of the epoxides with the formation of carbonyl compounds [23,24].…”

Fabrication of Meso/Macroporous Carbon Monolith and its Application as a Support for Adsorptive Separation of D-Amino Acid from Racemates

“…[1][2][3][4] Many research efforts are currently focused on the production of optically pure products, due to increasing demands for drugs which may be administered in optically pure forms. [5][6][7] Among this category of drugs, chiral amino acids and alcohols are important and widely utilized intermediates for the synthesis of a variety of biologically active molecules. In the last few decades, numerous efforts have been devoted to the synthesis and isolation of chiral amino acids.…”