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Marek Figlus

RECOVERABLE CATALYSTS FOR ASYMMETRIC REDUCTION OF IMINES


SYNTESIS AND EVALUATION OF ACTIVITIES
2010. 184 S.
Verlag/Jahr: VDM VERLAG DR. MÜLLER 2010
ISBN: 3-639-25071-0 (3639250710)
Neue ISBN: 978-3-639-25071-8 (9783639250718)

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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.
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