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Title: Organocatalysts for the asymmetric reduction of aromatic ketimines with trichlorosilane
Author: MacDougall, Kenneth N.
ISNI:       0000 0004 2669 6800
Awarding Body: University of Glasgow
Current Institution: University of Glasgow
Date of Award: 2008
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Asymmetric reduction of N-aryl ketimines 189a j, 212, and 213 with trichlorosilane can be catalyzed by new N-methyl L-amino acid-derived Lewis-basic organocatalysts, such as bisamide 197c (10 mol%), in toluene at room temperature with high enantioselectivity (≤92% ee). The structure-reactivity investigation shows that the product configuration is controlled by the nature of the side chain of the catalyst scaffold (e.g., i Pr vs Me, as in 197c and 208c), so that catalysts of the same absolute configuration may induce the formation of the opposite enantiomers of the product. Arene-arene interactions between the catalyst and the incoming imine appear to be the prerequisite for asymmetric induction. This metal-free, organocatalytic protocol is competitive with the traditional, metal-catalyzed methodology.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry