Regio- and stereo-selective ring opening of epoxides with amide cuprate reagents

Abstract

Amide cuprate reagents attack the less hindered carbon atom of epoxides to give 1,2-amino alcohols in good yields; this procedure is applied to the synthesis of an aziridine alcohol bearing a carborane framework which is a potentially useful 1 O B carrier for boron neutron capture therapy.

Comparative Study of Regioselective Synthesis of β-Aminoalcohols under Solventless Conditions Catalyzed by Sulfated Zirconia and SZ/MCM-41

“…The classical approach for the synthesis of β-aminoalcohols, involving nucleophilic opening of epoxides by amines requires heat treatment and requires an excess of amine. Several catalysts have been utilized in these reactions: montmorillonite [16], Ti(o-i-Pr) 4 [17], SmI 2 , [18] basic metal amides, [19] SmCl 3 [20], metal triflates such as Sn(OTf) 2 , Cu(OTf) 2 , LiOTf and Yb(OTf) 3 [21], ammonium decatungstocerate (IV) [22], RuCl 3 [23], zirconium (IV) chloride [24], cyclodextrins [25] and also CeCl 3 [26], silica-gel [27], alumina [28], ionic liquids [29], water [30] We have successfully used sulfated zirconia for Biginelli condensation reactions, [35] for the Paal Knorr reaction in the synthesis of tetrahydroindolone derivatives [36] and for the acylal protection and deprotection reactions [37]. In this paper we have synthesized, characterized and evaluated sulfated zirconia and SZ/MCM-41 in the oxirane opening with amines to obtain β-aminoalcohols under mild, solventless conditions.…”

Study of catalytic activity of a polymer‐supported Ce catalyst for the synthesis of biofuels and β‐amino alcohol derivatives under ambient condition

“…But deficiency of selectivity, requirement of excess amine and high temperature in the traditional method lead to the requirement of activation of epoxide by suitable catalyst to increase their impressibility to nucleophilic attack by amine. A preliminary study shows many methodologies had been reported earlier for the production of β‐amino alcohol derivatives, which includes the use of metal amides, transition metal halides, metal alkoxides, rare earth metal halides, metal triflates, alumina, alkali metal perchlorates, and silica under high pressure . The earlier reported synthetic methodologies have many disadvantages such as low yield of product, elevated temperature, expensive catalyst preparation pathway, moisture sensitive catalyst, and extended reaction time requirement.…”

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.…”