210408-13-2

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Relevant academic research and scientific papers

Enantioselective desymmetrization of meso epoxides with anilines catalyzed by a niobium complex of a chiral multidentate binol derivative

Molecular recognition in the desymmetrization of meso epoxides with anilines is displayed by a Lewis acid catalyst formed from niobium(V) methoxide and a novel tetradentate binol derivative. The catalyst has a remarkable ability to distinguish between dif

Asymmetric Catalytic Syntheses of Pharmaceutically Important β-Amino-α-Hydroxyl Esters by Enantioselective Aminolysis of Methyl Phenylglycidate

Chiral macrocyclic CrIII salen complexes have been synthesized, characterized, and used as catalysts in the asymmetric aminolysis of aromatic ester epoxides with various anilines to prepare the β-amino-α-hydroxyl esters in very good yield (up t

Synthesis of chiral ligands with multiple stereogenic centers and their application in titanium(iv)-catalyzed enantioselective desymmetrization of meso-epoxides

New chiral ligands, (S,R,S)-1, (S,S,S)-1, (S,S,R)-1, (S,R,R)-1, (R,R,R)-1, (R,R,S)-1, (R,S,S)-1, (R,S,R)-1, (S,R,S)-2, (S,S)-3 and (R,S)-4 with diverse stereogenic centers arising from various diastereomeric combinations of aminoalcohol functionality with

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.

Enantioselective desymmetrization of meso-epoxides with anilines catalyzed by polymeric and monomeric Ti(IV) salen complexes

The active catalysts for the enantioselective ring opening (ARO) of meso-stilbene oxide, cis-butene oxide, cyclohexene oxide, cyclopentene oxide, and cyclooctene oxide with various substituted anilines were generated in situ by the reaction of Ti(Oi

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.

Zn(ii)-catalyzed desymmetrization of meso-epoxides by aromatic amines in water

The Zn(OTf)2-SDS-bipyridine 1 system has proved to be an effective catalyst in water for the desymmetrization of ep-oxides 2a-d by anilines 3a-d. After obtaining comparable results by using Sc(III)-SDS and Zn(II)-SDS systems in the case of 2a and 3a, we h

Highly enantioselective syntheses of chiral β-amino alcohols in the presence of chiral TiIV Schiff base complexes as catalysts

Two new chiral Schiff bases 1 and 2 were prepared by condensation of 3,3′-di-tert-butyl-5,5′-methylenebis(salicylaldehyde) and 3,3′-dimethyl-5,5′-methylenebis(salicylaldehyde) with (1R,2S)-(-)-2-aminodiphenylethanol and were characterized by elemental ana

Scandium-bipyridine-catalyzed enantioselective aminolysis of meso-epoxides

The scandium-bipyridine-catalyzed enantioselective addition of anilines and O-alkyl hydroxylamines to meso-epoxides has been optimized and extended to a broad range of epoxides and amines. Whereas aromatic meso-epoxides generally furnished the corresponding 1.2-amino alcohols in Excellent enantioselectivities, aliphatic meso-epoxides only gave rise to moderate enantioselectivities in the aminolysis. The catalyst loading may be lowered to just 5 mol% with only marginal effects on yield and enantioselectivity. A strong positive nonlinear effect has been observed, pointing to aggregation phenomena of the catalyst.

The development of scalemic multidentate niobium complexes as catalysts for the highly stereoselective ring opening of meso-epoxides and meso-aziridines

The discovery and development of a new Lewis acid system based on a complex formed from niobium(V) methoxide and (R)-3,3′-bis(2-hydroxy-3- isopropylbenzyl)-1,1′-binaphthalene-2,2′-diol, a novel tetradentate BINOL derivative, is presented. The system was s