Brønsted Acid‐Catalysed Epoxide Ring‐Opening Using Amine Nucleophiles: A Facile Access to <i>β</i>‐Amino Alcohols
Aparna Tyagi, Naveen Yadav, Jabir Khan, Sankalan Mondal, Chinmoy Kumar Hazra
Abstract
A mild, efficient, and metal-free synthetic protocol for the synthesis of β-amino alcohols is reported. The reaction proceeds at room temperature with only 0.5 mol % catalyst loading and affords β-amino alcohol derivatives in excellent yield. This protocol is well-tolerated by a wide range of styrene oxide and aniline derivatives. A notably efficacious gram-scale synthesis is also reported with a high TON=842. Further, the Hammett correlation study was also performed to identify the rate-determining step.
Topics & Concepts
EpoxideNucleophileAnilineChemistryYield (engineering)CatalysisAmine gas treatingStyrene oxideAlcoholRing (chemistry)Brønsted–Lowry acid–base theoryCombinatorial chemistryAmino acidOxideOrganic chemistryStyreneMedicinal chemistryMaterials scienceCopolymerPolymerBiochemistryMetallurgyChemical Synthesis and AnalysisChemical Synthesis and ReactionsSynthesis and Catalytic Reactions