New organocatalysts for the asymmetric reduction of imines with trichlorosilane

Malkov, A. V., Vrankova, K., Sigerson, R. C., Stoncius, S. and Kocovsky, P. (2009) New organocatalysts for the asymmetric reduction of imines with trichlorosilane. Tetrahedron, 65(45), pp. 9481-9486. (doi: 10.1016/j.tet.2009.08.048)

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Abstract

Asymmetric reduction of prochiral ketimines 1a-f with trichlorosilane can be catalyzed by the Lewis-basic formamides (S)-4a,b, derived from N-methyl valine, with <91% enantioselectivity and low catalyst loading (<= 5 mol %) at room temperature in toluene. .

Item Type:Articles
Keywords:AMINO ACID-DERIVATIVES Asymmetric catalysis Asymmetric reduction CATALYZED TRANSFER HYDROGENATION DYNAMIC KINETIC RESOLUTION Enantioselective reduction EXPERIMENTAL SUPPORT HIGHLY ENANTIOSELECTIVE HYDROGENATION Hydrosilylation HYDROXYCYCLOPENTADIENYL RUTHENIUM HYDRIDE IR-F-BINAPHANE Lewis-basic catalysts N-ARYL IMINES Organocatalysis ORGANOCATALYSTS REDUCTION ROOM-TEMPERATURE STEREOSELECTIVE REDUCTION TEMPERATURE Trichlorosilane UNPRECEDENTED SUBSTRATE PROFILE
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Malkov, Dr Andrei and Stoncius, Mr Sigitas and Kocovsky, Professor Pavel
Authors: Malkov, A. V., Vrankova, K., Sigerson, R. C., Stoncius, S., and Kocovsky, P.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron
ISSN:0040-4020

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
370221New organocatalysts from amino acids exploitation of Chiral Relay and Aromatic Interactions in Asymmetric CatalysisAndrei MalkovEngineering & Physical Sciences Research Council (EPSRC)GR/S87294/01Chemistry