1135586-85-4

Upstream product

• 28128-12-3 (methyl)(phenyl)aminoacetone 
• 62-53-3 aniline 
• 925669-95-0 2,3-cis-epoxybutane 
• 1758-32-3 2,3-epoxybutane 
• 21490-63-1 2,3-trans-epoxybutane 

Relevant academic research and scientific papers

Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: Application for the synthesis of an enantiopure oxazolidine ring

New recyclable chiral salen complexes Cr(iii)1-7 were synthesized from various macrocyclic chiral ligands having multistereogenic chiral centers which work synergistically to give the best results in terms of the enantioselectivity and yield of the products. Among the synthesized complexes, the Cr(iii)-4 salen complex efficiently catalyzed the ring opening reaction of various aromatic ester epoxides, trans-epoxides and meso-epoxides with anilines to furnish the corresponding β-amino-α-hydroxyl esters and β-amino alcohols with an excellent ee of up to 99% and a high yield of up to 95%. Furthermore, the chirally pure β-amino-α-hydroxyl esters were converted into pharmaceutically important oxazolidine ring systems. Moreover, the chromium catalyst was recycled up to 5 cycles with the retention of its activity.

Catalytic enantioselective Amadori-Heyns rearrangement of racemic α-hydroxy ketones with arylamines: Synthesis of optically active α-arylamino ketones

A novel synthesis of optically active α-arylamino ketones through an organocatalytic enantioselective Amadori-Heyns rearrangement is described. The Royal Society of Chemistry 2013.

Synthesis of enantiopure β-amino alcohols via AKR/ARO of epoxides using recyclable macrocyclic Cr(III) salen complexes

A series of chiral macrocyclic Cr(III) salen complexes 1-8 were synthesized and characterized. These complexes were found to be highly active, regio-, diastereo-, and enantioselective catalysts in aminolytic kinetic resolution (AKR) of racemic trans-epoxides as well as asymmetric ring opening (ARO) of prochiral meso-epoxides with various anilines as nucleophiles at room temperature in 18-24 h. Excellent yields (>99% with respect to the nucleophile) with high enantioselectivity (ee, >99%) of chiral anti-β-amino alcohols was achieved with concomitant recovery of corresponding epoxides in high ee (up to >99%). The complex 1 also catalyzed the ARO of meso-epoxides to provide corresponding syn-β-amino alcohols in high yield (99%) and ee (up to 91%). Due to built-in basic sites in the catalyst, no external base (as an additive) was required to promote AKR and ARO reactions. The catalyst 1 was conveniently recycled several times with retention of its performance. The AKR of trans-stilbene oxide with aniline was successfully demonstrated at relatively higher scale (10 mmol) using the catalyst 1.

Reusable chiral dicationic chromium(III) salen catalysts for aminolytic kinetic resolution of trans-epoxides

A series of new recyclable chiral dicationic chromium(III) salen complexes 1-10 bearing different substituents, viz., hydrogen, methyl, tert-butyl, triphenylphosphinomethyl, triethylaminomethyl, methylimidazolium, methylpyridinium, methyl-N,N-dimethylpyri

Chiral zinc(II) and copper(II)-catalyzed asymmetric ring-opening reactions of meso-epoxides with aniline and indole derivatives

The ring-opening reactions of meso-epoxides with aniline and indole derivatives proceeded smoothly in water in the presence of Zn(II) and Cu(II) surfactant-type catalysts to afford the corresponding products in moderate to high yields with good to excelle