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

Abstract

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

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Publication details

The article was received on 14 Jun 2018, accepted on 07 Aug 2018 and first published on 07 Aug 2018


Article type: Paper
DOI: 10.1039/C8NJ02960A
Citation: New J. Chem., 2018, Accepted Manuscript
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    Development of recyclable chiral macrocyclic metal complexes for asymmetric aminolysis of epoxides: application for the synthesis of enantiopure oxazolidine ring

    R. Tak, M. Kumar, M. Nazish, T. Menapara, R. I. Kureshy and N. H. Khan, New J. Chem., 2018, Accepted Manuscript , DOI: 10.1039/C8NJ02960A

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