Synthesis ofC₂-Symmetric Chiral Amino Alcohols: Their Usage as Organocatalysts for Enantioselective Opening of Epoxide Ring

Asymmetric Organocatalytic Efficiency of Synthesized Chiral β-Amino Alcohols in Ring-Opening of Glycidol with Phenols

“…We have demonstrated that the chiral b-amino alcohols are efficient enantioselective organocatalysts for kinetic resolution of racemic glycidol with phenols [36]. However, the enantioselectivities of amino alcohol organocatalysts were obtained drastically different with respect to the phenol nucleophiles.…”

“…We also showed that the reaction conditions have a strong influence on the yield and enantioselectivity of the reaction; no significant reactions occurred when performed at the room temperature to the studied temperature (50°C). The higher temperatures and further reaction periods lead to higher yields but lower enantioselectivities [36]. Encouraged by these observations, we aimed to practically route to synthesise of chiral b-amino alcohols as efficient organocatalysts.…”

“…In our previous study, it was found that chiral b-amino alcohols effectively catalyzed the asymmetric ring opening of glycidol with phenols [36]. To the best of our knowledge, this was the first example to have been reported in the literature.…”

Theoretical and Experimental Studies on the Regioselectivity of Epoxide Ring Opening by Nucleophiles in Nitromethane without any Catalyst: Nucleophilic-Chain Attack Mechanism

“…It is commonly recognised that the epoxide ring-opening reaction under basic or neutral conditions proceeds via the S N 2 mechanism, but under acidic conditions, a borderline S N 2 mechanism has been invoked to justify the electronic pull on the oxygen by an acid [1,2]. Furthermore, the ring opening of epoxides is an important method of forming alcohols [26]. Consequently the introduction of new methods for the nucleophilic ring-opening of epoxides that work under appropriate conditions is important.…”

A biocatalytic approach for regioselective monoacetylation of 3-aryloxy-1,2-propanediols by porcine pancreatic lipase

“…Other extensive applications include preservatives in cosmetics and foods [5], gene therapy [6], optics [7], pigmented ink [8], polyesters [9], resins [10], dyes [11], and nonspreading lubricants [12]. 3-Aryloxy-1,2-propanediols are also often used as intermediates in the synthesis of chiral ligands for transition metal complexes or building blocks for crown ethers and many other synthetic sequences [13,14]. It is necessary to synthesize these molecules in optically pure form as chirality governs the major biological interactions.…”