1186336-25-3Relevant academic research and scientific papers
Enantioselective reduction of: N -alkyl ketimines with frustrated Lewis pair catalysis using chiral borenium ions
Mercea, Dan M.,Howlett, Michael G.,Piascik, Adam D.,Scott, Daniel J.,Steven, Alan,Ashley, Andrew E.,Fuchter, Matthew J.
, p. 7077 - 7080 (2019/06/20)
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.
1,1′-Binaphthyldiamine-based lewis bases as readily available and efficient grganocatalysts for the reduction of N-Aryl and N-Alkyl ketimines
Guizzett, Stefania,Benaglia, Maurizio,Celentano, Giuseppe
experimental part, p. 3683 - 3687 (2009/12/03)
The development of simple, low-cost, efficient, and sustainable routes to enantiomerically pure amines is a topic of extraordinary interest, specially in view of future industrial applications. In this context, we wish to report a chemical and stereochemical efficient synthesis of chiral amines through the Lewis base activated trichlorosilane reduction of ketimines. An organocatalyst, easily prepared in a single step through the condensation of picolinic acid and commercially available 1,1′-binaphthyldiamine, is the key element of this metal-free methodology, that allowed the synthesis of chiral secondary and primary amines in high yields and stereose-lectivity. Noteworthy, such catalysts are able to promote the reduction of N-alkyl ketimines, often in quantitative yield and up to 87% enantioselectivity; it: is worth mentioning that for such transformations only one other organocatalytic system has been reported so far.
