Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines
journal contributionposted on 08.08.2014 by Andrei Malkov, Angus J.P. Stewart-Liddon, Grant D. McGeoch, Pedro Ramirez-Lopez, Pavel Kocovsky
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A new family of Lewis basic 2-pyridyl oxazolines have been developed, which can act as efficient organocatalysts for the enantioselective reduction of prochiral aromatic ketones and ketimines with trichlorosilane, a readily available and inexpensive reagent. 1-Isoquinolyl oxazoline, derived from mandelic acid, was identified as the most efficient catalyst of the series, capable of delivering high enantioselectivities in the reduction of both ketones (up to 94% ee) and ketimines (up to 89% ee).
We thank the EPSRC for grant No. GR/S87294/01, GSK and EPSRC for an industrial CASE awards to A. J. P. S. L., the Ministry of Education and Science of Spain for a fellowship to PR-L, the Loughborough University, the University of Glasgow and Dr. Alfred Bader for additional support.