Enantioselective reduction of -alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions

Enantioselective reduction of ketimines was demonstrated using chiral N -heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N -alkyl substituents. Comparative reactivity and mechan...

Full description

Saved in:
Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-06, Vol.55 (49), p.777-78
Main Authors: Mercea, Dan M, Howlett, Michael G, Piascik, Adam D, Scott, Daniel J, Steven, Alan, Ashley, Andrew E, Fuchter, Matthew J
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Enantioselective reduction of ketimines was demonstrated using chiral N -heterocyclic carbene (NHC)-stabilised borenium ions in frustrated Lewis pair catalysis. High levels of enantioselectivity were achieved for substrates featuring secondary N -alkyl substituents. Comparative reactivity and mechanistic studies identify key determinants required to achieve useful enantioselectivity and represent a step forward in the further development of enantioselective FLP methodologies. Effective enantioselective reduction of ketimines has been demonstrated by 'frustrated' Lewis pair catalysis using an IBiox-stabilised borenium cation.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc02900a