Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines

Kathuria, L and Samuelson, AG (2021) Chiral N-heterocyclic carbene-iridium complexes for asymmetric reduction of prochiral ketimines. In: Polyhedron, 195 .

	PDF Pol_195.pdf - Published Version Restricted to Registered users only Download (2MB) | Request a copy
	PDF IrLeuMe_233ir_CheckCIF.pdf - Published Supplemental Material Restricted to Registered users only Download (252kB) | Request a copy
	PDF IrPGMe_235ir_CheckCIF.pdf - Published Supplemental Material Restricted to Registered users only Download (243kB) | Request a copy
	PDF IrValTMB_lk574_CheckCIF.pdf - Published Supplemental Material Restricted to Registered users only Download (217kB) | Request a copy
	PDF L3_lk233_CheckCIF.pdf - Published Supplemental Material Restricted to Registered users only Download (235kB) | Request a copy
	Microsoft Word 1-s2.0-S0277538720306331-mmc1.docx - Published Supplemental Material Download (4MB)

Abstract

Enantioselective reduction of imines to the corresponding chiral secondary amines has been studied using a series of chiral half-sandwich iridium complexes. Chiral N-heterocyclic carbene (NHC) ligands in these complexes were synthesized from readily available, naturally occurring amino acids. Inexpensive phenylsilane was used as a convenient hydrogen donor. Under the optimized conditions, Ir-NHC complexes could reduce ketimines in good yields, albeit with moderate enantiomeric excess (ee). The phenylglycine derived chiral NHC was shown to give the best Ir catalyst and it also gave the maximum ee compared to catalysts prepared from other NHCs in this series. The opposite enantiomer of the reduction product was always obtained while using the Ir complex bearing a valine based NHC. The yields were consistently high with a variety of imine substrates having different steric and electronic demands. © 2020

Item Type:	Journal Article
Publication:	Polyhedron
Publisher:	Elsevier Ltd
Additional Information:	Copyright to this article belongs to Elsevier Ltd
Department/Centre:	Division of Chemical Sciences > Inorganic & Physical Chemistry
Date Deposited:	12 Feb 2021 09:38
Last Modified:	12 Feb 2021 09:38
URI:	http://eprints.iisc.ac.in/id/eprint/67514

Actions (login required)

View Item