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Synfacts 2006(4): 0386-0386  
DOI: 10.1055/s-2006-932098
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York

Organocatalytic Asymmetric Hydrosilylation of Ketones and Ketimines

Contributor(s): Benjamin List, Daniela Kampen
A. V. Malkov*, A. J. P. Stewart Liddon, P. Ramírez-López, L. Bendová, D. Haigh, P. KoČovsk*
University of Glasgow and GlaxoSmithKline Pharmaceuticals, Stevenage, UK
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Publikationsverlauf

Publikationsdatum:
24. März 2006 (online)

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Significance

Organocatalytic asymmetric hydrosilylations are reported. Chiral isochinolyloxazoline 1 mediates the reduction of both aromatic ketones 2 and aromatic ketimines 4 with trichlorosilane to give the corresponding alcohols 3 and amines 5 in good yields and enantioselectivities. Mechanistic considerations based on the interpretation of experimental data and computational investigations are also provided. The observed chiral induction is presumed to result from aromatic interactions between catalyst 1 and prochiral substrates 2 and 4.