YCl3-Catalyzed Highly Selective Ring Opening of Epoxides by Amines at Room Temperature and under Solvent-Free Conditions

Abstract

A simple, efficient, and environmentally benign approach for the synthesis of β-amino alcohols is herein described. YCl 3 efficiently carried out the ring opening of epoxides by amines to produce β-amino alcohols under solvent-free conditions at room temperature. This catalytic approach is very effective, with several aromatic and aliphatic oxiranes and amines. A mere 1 mol % concentration of YCl 3 is enough to deliver β-amino alcohols in good to excellent yields with high regioselectivity.

Yttrium-Catalyzed Regioselective Aminolysis of 2,3-Epoxy Esters and Amides

“…Herein, we report a catalytic version of the regioselective aminolysis of 2,3-epoxy esters and amides with the carbonyl moiety as the orienting group, which is efficiently catalyzed by yttrium triflate, affording a series of α-hydroxy β-amino esters and amides in regioisomerically pure forms (Scheme 1 B). 9…”

Synthesis of β-amino alcohols by ring opening of epoxides with amines catalyzed by sulfated tin oxide under mild and solvent-free conditions

“…16 Better techniques have recently been discovered for this transformation. [17][18][19][20][21][22][23][24][25][26] These protocols do have certain drawbacks, though, like lengthy reaction times, high temperatures, poor regioselectivity, moderate yields, the need for stoichiometric amounts of catalyst and reagent, the possibility of allylic alcohol rearrangement, the potential dangers associated with handling moisture-sensitive reagents during catalyst preparation, and the fact that they are typically limited to aromatic amines.…”

Ring-Opening of Epoxides with Amines for Synthesis of β-Amino Alcohols in a Continuous-Flow Biocatalysis System

“…The asymmetric ring-opening (ARO) reaction of epoxides with amines is the most straightforward route to prepare β-amino alcohols. In recent years, several catalysts such as Lewis acids [11][12][13], metal-organic frameworks [14] and Bismuth (III) salts [15][16][17][18] have been reported for ring-opening reactions. However, these approaches usually require the use of costly reagents, high catalyst loadings, poor regioselectivity and also entail side effects, such as the rearrangement of epoxides to allyl alcohols under strong alkaline conditions or polymerization under strongly acidic conditions.…”