Issue 9, 2016

Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(iii) metal complex

Abstract

An efficient asymmetric desymmetrization of meso-epoxides with anilines catalysed by a series of simple and environmentally benign in situ generated Fe(III) complexes based on chiral tridentate ligands L1–L7 with achiral and chiral linkers (methylene, piperazine, R/S BINOL and diethyl tartrate) was carried out at rt. The in situ generated iron metal complex based on ligand L5a emerged as improved (low catalyst loading) catalyst for asymmetric desymmetrization of meso-epoxides with anilines giving high enantioselectivity (up to 99%) and high yield (95%) of enantiopure β-amino alcohols in 14 h. While excellent results for ARO of cyclic as well as aliphatic epoxides with anilines was achieved with in situ generated complex from the ligand L4h and Fe(III) chloride, the catalyst was recoverable and recyclable (five times) with retention of its performance.

Graphical abstract: Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(iii) metal complex

Supplementary files

Article information

Article type
Paper
Submitted
09 Nov 2015
Accepted
09 Jan 2016
First published
14 Jan 2016

RSC Adv., 2016,6, 7693-7700

Author version available

Enantioselective syntheses of β-amino alcohols catalyzed by recyclable chiral Fe(III) metal complex

R. Tak, M. Kumar, R. I. Kureshy, M. K. Choudhary, N. H. Khan, S. H. R. Abdi and H. C. Bajaj, RSC Adv., 2016, 6, 7693 DOI: 10.1039/C5RA23600B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements