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.

Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives / M. Bonsignore, M. Benaglia, L.M. Raimondi, M. Orlandi, G. Celentano. - In: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1860-5397. - 9(2013 Mar 02), pp. 633-640. [10.3762/bjoc.9.71]

Enantioselective reduction of ketoimines promoted by easily available (S)-proline derivatives

M. Bonsignore;M. Benaglia;L.M. Raimondi;M. Orlandi;G. Celentano
2013-03-02

Abstract

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.
chiral prolines ; imine reduction ; Lewis bases ; organocatalysis ; trichlorosilane
Settore CHIM/06 - Chimica Organica
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/221285
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