Enantioselective reduction of N-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 mechanis...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-05, Vol.55 (49), p.7077-7080
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
Subjects:
Catalysis
Crystallography
Enantiomers
Imines
Reduction
Substrates
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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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c9cc02900a