RECOVERABLE CATALYSTS FOR ASYMMETRIC REDUCTION OF IMINES

Obtaining chiral amines from ketones via imine intermediates represents an attractive strategy that opens a straightforward route to valuable building blocks for the pharmaceutical and other fine chemicals industries. Metal-free oranocatalysis can be viewed as an attractive and broadly applicable methodology in which the metal is not vital for the key bond-forming event. N-methylvaline-derived formamides proved to be efficient catalysts for asymmetric reduction of prochiral ketimines with trichlorosilane, (up to 98%, 95% ee). Tagging the catalyst to a fluorous ponytail, soluble and insoluble polymers, or gold nanoparticles simplified the isolation procedure, while preserving high activities and stereoselectivities (up to 98%, 91% ee). The recovered catalysts could be reused at least 5 times without the loss of activity or stereoselectivity. This technology appears to be particularly suited to the small-scale parallel chemistry.

Autorentext

1998-2003 - Technical University of Lodz/Ghent University, M.Sc. degree. 2003-2005 - Medical University of Lodz, Research Assistant. 2005-2008 - Glasgow University/New York State University at Stony Brook, Doctoral research. 2008 - To date - Glasgow University/GlaxoSmithKline, Postdoctoral Research Assistant