%0 Journal Article
%T Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives
%A Martina Bonsignore
%A Maurizio Benaglia
%A Laura Raimondi
%A Manuel Orlandi
%J Beilstein Journal of Organic Chemistry
%D 2013
%I 
%R 10.3762/bjoc.9.71
%X The behavior of readily synthesized and even commercially available (S)-proline derivatives, was studied in the trichlorosilane-mediated reduction of ketoimines. A small library of structurally and electronically modified chiral Lewis bases was considered; such compounds were shown to promote the enantioselective reduction of different substrates in good chemical yields. In the HSiCl3 addition to the model substrate N-phenylacetophenone imine, the organocatalyst of choice led to the formation of the corresponding amine with good stereoselectivity, up to 75% ee. Theoretical studies were also performed in order to elucidate the origin of the stereoselection.
%K chiral prolines
%K imine reduction
%K Lewis bases
%K organocatalysis
%K trichlorosilane
%U http://dx.doi.org/10.3762/bjoc.9.71