Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2006(4): 0386-0386
DOI: 10.1055/s-2006-932098
DOI: 10.1055/s-2006-932098
Bioorganic Chemistry and Organocatalysis
© Georg Thieme Verlag Stuttgart · New York
Organocatalytic Asymmetric Hydrosilylation of Ketones and Ketimines
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
Further Information
Publication History
Publication Date:
24 March 2006 (online)
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.