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Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines

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journal contribution
posted on 08.08.2014 by Andrei Malkov, Angus J.P. Stewart-Liddon, Grant D. McGeoch, Pedro Ramirez-Lopez, Pavel Kocovsky
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).

Funding

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.

History

School

  • Science

Department

  • Chemistry

Published in

Organic and Biomolecular Chemistry

Volume

10

Issue

25

Pages

4864 - 4877

Citation

MALKOV, A.V. ... et al., 2012. Catalyst development for organocatalytic hydrosilylation of aromatic ketones and ketimines. Organic and Biomolecular Chemistry, 10 (25), pp. 4864-4877.

Publisher

© Royal Society of Chemistry

Version

AM (Accepted Manuscript)

Publication date

2012

ISSN

1477-0520

eISSN

1477-0539

Language

en

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