Role of noncovalent interactions in the enantioselective reduction of aromatic ketimines with trichlorosilane.
[reaction: see text] Asymmetric reduction of ketimines 1 with trichlorosilane can be catalyzed by a new N-methyl L-valine derived Lewis basic organocatalyst, such as 4d, with high enantioselectivity. The structure-reactivity investigation suggests hydrogen bonding and arene-arene interactions between the catalyst and the incoming imine as the main factor determining the enantiofacial selectivity.
Malkov
Andrei V
AV
Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, U.K. amalkov@chem.gla.ac.uk
Mariani
Andrea
A
MacDougall
Kenneth N
KN
Kocovský
Pavel
P