Synthesis of an Advanced Precursor of Rivastigmine : Cinchona-derived Quaternary Ammonium Salts as Organocatalysts for Stereoselective Imine Reductions
Articolo
Data di Pubblicazione:
2015
Citazione:
Synthesis of an Advanced Precursor of Rivastigmine : Cinchona-derived Quaternary Ammonium Salts as Organocatalysts for Stereoselective Imine Reductions / A. Genoni, M. Benaglia, E. Mattiolo, S. Rossi, L. Raimondi, P. C. Barrulas, A.J. Burke. - In: TETRAHEDRON LETTERS. - ISSN 0040-4039. - 56:42(2015 Oct 14), pp. 5752-5756.
Abstract:
The enantioselective reduction of ketoimines has been successfully realized, using trichlorosilane as the stoichiometric reducing agent in the presence of catalytic amounts of a Lewis base, specifically a Cinchona derivative. For the first time, a novel class of derivatives was studied, featuring a picolinamide unit bound to the alkaloid scaffold, further functionalized as quaternary ammonium salt at the quinuclidine ring. Excellent yields and from good to high enantioselectivities (up to 92% ee) were obtained in the reduction of ketoimines. The novel catalysts were successfully employed in the synthesis of an enantiomerically pure advanced precursor of the blockbuster drug Rivastigmine.
Tipologia IRIS:
01 - Articolo su periodico
Keywords:
Ketoimine reduction; Chiral amines; Cinchona alkaloid derivatives; Rivastigmine; Trichlorosilane
Elenco autori:
A. Genoni, M. Benaglia, E. Mattiolo, S. Rossi, L. Raimondi, P. C. Barrulas, A.J. Burke
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